Vacation Home Rentals By Owner In Bridgton, ME

$539.27

Bridgton Bungalow | Brand New, Central & Spacious

Bridgton, Maine, United States

Welcome to The Bridgton Bungalow! Our 4 bedroom 3 full bathroom was built in 2022 and is the perfect getaway for large families to make some memories that will last forever. Our home has modern construction, TVs in every room + a beautiful open space living room. Situated at the end of a quiet residential street our home is secluded and very peaceful yet only 10 min. from Downtown Naples and downtown Bridgton. Only 10 min. to Pleasant Mt. and multiple lakes, our home is perfect for any season!brbrWE ARE LOCAL - Just let us know what you needbrbrOur home is located at the end of a very quiet neighborhood street.brOur rules are pretty simple. Treat our home as if it was yours.br- Guest making the reservation must be over 25. All guests must be over 25 if not part of a family. This is non negotiable. Please do not book if everyone in your group is not 25+ years old.br- No smoking in the housebr- The number of guests requested on the booking is the max amount allowed to spend the night.br- A rental agreement may be provided with more specific rules and information.br- Quiet time is from 10pm-8am (inside and outside of the house)br- NO loud music or noise will be toleratedbr- Respect the neighbors

5

Bed

3

Bath

12

Sleeps

$642.9

/ Nightly

Private Vacation Home

New for 2026! Cozy Lakeside Retreat Nestled in the Woods on Long Lake

Bridgton, Maine, United States

New for 2026! This inviting 3-bedroom, 2-bathroom home on Long Lake offers the perfect blend of cozy comfort and modern convenience. Thoughtfully designed for a relaxing getaway, the home features a fully equipped kitchen for easy meals and a comfortable living space ideal for gathering after a day on the water. A peaceful enclosed porch provides a wonderful spot to unwind, sip your morning coffee, or enjoy the gentle lakeside breeze while surrounded by nature.brbrOutside, a cleared path leads through the trees leading directly to the waterfront and private dock. Cement steps provide easy access into deep water, making it an excellent spot for swimming. Guests are welcome to bring a boat up to 16’ to keep at the dock, or take advantage of the provided paddleboard to explore Long Lake at a leisurely pace. Ideally located, this home offers a quiet lakeside retreat while still being just a short drive to the shops, dining, and attractions of Bridgton and Harrison—making it a perfect family-friendly escape.brbr* Sheets, pillowcases, beach towels, and bath towels not provided *brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

Bed

Bath

Sleeps

$3633.49

/ Nightly

Private Vacation Home

40-acre Luxury Beach Front Estate-Ideal for Reunions & Retreats

Bridgton, Maine, United States

This spectacular, 40-acre estate is located on clear, warm Highland Lake in Bridgton, Maine, halfway between the Atlantic Ocean and the White Mountains of New Hampshire. The extensive grounds provide a private, peaceful, park-like setting which fosters relaxation and engenders a sense of well-being. The property includes more than 1,000 feet of mainland waterfront with two sandy beaches, part of a small nearby island, a two-story boathouse with a 2nd floor activity center (originally the estate's ballroom), a 52-foot pier, a clay tennis court, a grass volleyball/badminton court, three large sports fields, extensive woods, wildlife, and thousands of flowering plants. brbrNawandyn Estate is a unique property, more akin to a private resort than a vacation rental. In contrast to other vacation rentals, we offer a wide range of activities on site and tailor our property and to the needs and desires of each rental group. Guests may (1) choose whether they want a king or two twins in various bedrooms (perhaps an additional bed), (2) choose a preferred dining location, and (3) choose to cook for themselves, pick up food prepared by restaurants/lobster vendors/grocery stores, have meals catered and/or hire a private chef. The Owner is available to help you identify onsite and offsite activities that would appeal to individual members of your group. brbrWe have 15 years of experience optimizing the rental experience for our guests. Prior guests have described their Nawandyn Estate experiences as “magical” and “heaven.” Reviews of Nawandyn Estate are available under VRBO listing #328745. When VRBO converted to a booking site, it limited review postings to only those groups that used VRBO's website to pay for rentals. Reviews from groups that rent directly from Nawandyn Estate have been excluded.brbrNawandyn Estate has 16 bedrooms, including 4 bedrooms on the 1st floor. We tailor bedroom layouts to Renter’s wishes. If Renter wants more than 28 persons to sleep on the Estate, an “extra overnight guest fee” applies. As with any resort, a day fee applies to persons using the Estate but not paying to stay on the property.brbrThere are multiple rooms where your entire group may dine and/or socialize together in addition to numerous large outdoor venues. Your whole group can socialize and enjoy music in the huge living room with perfect acoustics and a grand piano. One dining room seats 28 (with overflow seating on the adjacent screened porch). The Event Center will accommodate everyone for dining, dancing, indoor games (e.g., classic games and mini pool), watching sports on a large smart TV, conducting meetings and/or otherwise socializing. There are also many places where individuals can enjoy time alone and places for small groups to gather. brbrNawandyn Estate makes available a multitude of activities on site which enable you to spend quality time with each other. Bring your swimsuit and favorite suntan lotion and let us provide beach towels, beach chairs, non-power watercraft, beach toys, fishing poles, etc. so you may kayak, paddle board, sunbathe on the swim raft, fish, float on foam mattresses, explore the lake and its islands, row a rowboat to a favorite fishing spot or throw your line off a pier, photograph wildlife, lounge on the beach, build sandcastles, play spike ball, count ducks, find frogs and turtles, etc. You can rent a power boat locally if you want to go water skiing, tubing, wake boarding, or cruising before you tie up your power boat at our 52-foot pier. When you need a break from the sun, you can play piano, ping pong, jenga, cards, chat or do puzzles in the boathouse activity center. Unlike other waterfront properties there are many activities available on land, including volleyball, badminton, tennis, softball, football, soccer, ultimate frisbee, corn hole, croquet and, nearby, golf. There are lots of opportunities on site or nearby to stroll, jog, bike (if you bring/rent one), hike or mountain climb. At Nawandyn, you can literally smell the flowers, listen to birds singing, star gaze, watch deer frolic, watch sunrises and sunsets, etc.brbrThere are three homes on the 40-acre Nawandyn Estate property, within a few-minute walk of a beach and there is a road that abuts the largest sandy beach for those who prefer to drive. Each residence has its own yard and is visually separated from the others, primarily by trees and other landscaping. Yet, the homes are close enough to together that children will hop, skip and jump across the lawn from one home to another. The property is fully furnished including all linens, books, cooking equipment, dishes, BBQ’s, etc. The first and largest home was built for an opera superstar, Olivia Fremstad, in 1915-16. The architect was John A. Gade, who had previously worked for the firm that designed the East and West Wings of the White House, the home of U.S. Presidents. Fremstad sold her property in 1926 to Eleazer Clark, a shipping and banking magnate, and his wife who immediately doubled the acreage, and added landscaping, the spectacular two-story boathouse and delightful Carriage House. Subsequently, a clay tennis court and Guest House were added. The Guest House was designed by Caleb Hornbostel, who beat Eero Saarinen and Louis Kahn to win the Museum of Modern Art’s first architectural contest. Clark’s grandson and granddaughter-in-law have recently restored and updated the property, adding among other things the Event Center, high-speed internet, A/C and heating via heat pump systems to the Guest House, Carriage House and the Event Center, and more gardens. Guests may rent the whole estate with its three residences via VRBO #328745 or half the estate either via VRBO #4864567 (Main House & Boathouse) or VRBO #4843806 (Guest House, Carriage House with Event Center).brbrNawandyn Estate is within several miles of two grocery stores including Hannaford Grocery, a seafood store, a specialty wine store, a specialty food store, a Reny’s department store, a book store, a women’s clothing and accessories store, several home décor and gift stores, several antique stores, a yarn shop, a bait and tackle shop, a beauty salon, a barbershop, a chocolate shop, two ice cream parlors, two banks, two gas stations, an EV charging station, at least 13 restaurants, two bars, a pub, an art gallery (representing about 40 artists), the “Rufus Porter Museum of Art and Ingenuity, a live music venue, a movie theater, a drive-in theater with two screens, a hospital, two urgent care centers, two pharmacies, an optician, and more. brbrVRBO now uses a defective artificial intelligence program to generate some content in its listings, resulting in false and/or misleading statements regarding distances, airports and significant local landmarks. The AI program misdirects prospective renters to airports that are NOT served by major airlines. Portland International Jetport (PWM) is the closest airport that is served by major airlines; it is just 42 miles from Nawandyn Estate (63 minutes via Routes 114 & 107). VRBO continually recategorizes details about listed properties which results in misleading information. To assure that prospective renters get correct information, Nawandyn Estate provides renters (in the Rental Agreement) with a four-page, single-spaced list of all the facilities, contents, and supplies available for renter use. brbrPlease let us know your group’s needs and desires, favorite activities, etc. We would like the opportunity to let you know how we propose to optimize your experience at Nawandyn Estate. brbrIn order to finalize a booking, you must fill in the blanks on our Rental Agreement that identify you, the size of your rental group, your rental purpose, all the potential members of your group (specifying the ages of children and any members that have mobility/health issues that need to be accommodated), sign both the Rental Agreement on page 10 and the “house rules” and liability lease form, and send it to the property Owners.

Bed

Bath

Sleeps

$570.38

/ Nightly

Private Vacation Home

Highland Lakefront Haven- Private Dock, Swim, Kayak and Views of Mt. Washington!

Bridgton, Maine, United States

Lakefront Getaway on Highland Lake – Bridgton, MEbrbrEscape to this charming year-round chalet on the shores of crystal-clear Highland Lake in Bridgton. Perfect for families or groups, this 4-bedroom, 3-bath home offers an ideal summer retreat with stunning lake views, plenty of space to relax, and direct water access. The house is also walking distance to downtown Bridgton with its restaurants, shopping, and entertainment venues.brbrThe open-concept Great Room and loft feature a wall of windows overlooking the lake, along with a large deck and screened porch for outdoor dining and lounging. On the main floor you’ll find two bedrooms and a full bath, a master suite upstairs with a queen bed, jet tub, and panoramic views, a loft with additional sleeping for 2 and a lower level with a bedroom, full bath, game/play area, and laundry.brbrEnjoy swimming, kayaking, boating, or simply floating in the clean, 1,400-acre lake. Hiking trails, charming local shops, restaurants, and all essentials are just a short walk away. North Conway and the White Mountains are a quick drive for day trips and more outdoor adventures.brbrWhether you're on the water, gathered around the firepit, or watching the sunset over Mt. Washington from the dock, this home is designed for summer memories.brbrThe home is directly across from the Noble House, so this is an ideal place to stay for weddings at that venue. brbrSleeps 8 | Wi-Fi | Washer/Dryer | Lakefront | Screened Porch | Large Deck | Firepit | Walk to townbrNote that linens and sheets are not included during summer rentals. For other times of the year linens and sheets need to be confirmed as available.brbrPlease be aware, our response rate appears low because we do not use the immediate booking process from VRBO. Your email inquiry will be received and responded to asap.brbrAlso, I have minimum night stay set to 7 days to ensure summer is rented for full weeks only. I can rent for 2-3 days outside of peak summer season.

4

Bed

3

Bath

8

Sleeps

$290.33

/ Nightly

Private Vacation Home

Private w/ waterfront <5 min to Pleasant Mt & town. Dock, pool table, ping-pong

Bridgton, Maine, United States

*** Update: The VRBO platform began auto-displaying a house description that currently reads Lakefront vacation home with kitchen and balcony. This text can't be edited or hidden. To ensure clarity for all guests, the house has private waterfront with a dock, a water pad, kayaks, a canoe, and other water gear at the water. The house is also set back from the water to comply with Maine waterfront laws for newer houses. Please see our photos, video links, and description in the listing for all details! ***brbrLooking for an easy, private getaway with your own waterfront A place surrounded by trees but around the corner from everything The vacation cabin feeling with modern amenities that make time away easy and more memorable brbrIn the summer, jump off the dock, paddle a canoe or kayak, go fishing, or relax with a book by the water on private Beaver Pond. Or use the Moose Pond public boat launch 3 minutes down the road. And it's only a 5 minute ride to the center of Bridgton for a movie or meal anytime of the year. brbrDuring the winter, wake up and be at Plesant Mountain ( Shawnee Peak ) for skiing or riding in less than 5 minutes. Go snow-shoeing or cross-country skiing on the snow-covered pond in back or on Moose Pond or the nearby trails. Or hit the snowmobile trails on and around Moose Pond and easily connect to the Maine state-wide trail system. brbrThis newer, comfortable 2 BR, 2BA house with private water frontage on Beaver Pond is nestled in the trees and has the extras that take stress out of getaways: br- Newer appliances, including a dishwasher, washer, dryer, full oven, refrigerator with ice maker, and filtered water systembr- Nighttime, winter, and rainy-day fun for all, with a full-sized pool table, ping pong, air hockey, board games, puzzles and toysbr- Screened-in porch accessible off the great room for reading or resting outsidebr- High-speed 2-gig fiber interne connection, satellite TV, and 4G mobile phone coverage inside or outside the housebrbrFull property details:brbr** Update: After years of allowing instant bookings, we've been forced to disable instant bookings due to a VRBO policy change that imposes significant cancellation fines on us in certain situations. We're sincerely sorry and all bookings will still be confirmed/accepted as quickly as possible after we receive them!**brbr- Waterfront: 160’ of private waterfront on Beaver Pond, with dock and cleared, private path to waterfront (See more here: https://www.instagram.com/reel/C8AdPMuhTSB or here: https://www.tiktok.com/@evergreenroadescapes/video/7378582862326500650)br- Close to it all: 5 minutes to Shawnee Peak for skiing or snowboarding, 5 minutes to downtown Bridgton, 2-3 minutes to Moose Pond public boat launch and nearby snowmobile trails.br- 2 bedrooms, including new master queen bed and newer, unique bunk-bed with single bed on top, double bed in the middle, and pull-out single trundle bedbr- Sleep up to 6 in beds; use the large couch or an air bed to sleep 7-8br- 2 full bathrooms, including master bathroombr- Great room including kitchen, dining, and living room areasbr- Kitchen including small center island and swivel chairs with backsbr- Large solid-wood dining room table that comfortably seats 8 and can fit 10-12br- Large sectional couch and 2 recliners in living room areabr- Screened in back porch with 2 outdoor recliners and bench overlooking trees and waterbr- 4-season: Baseboard heat, ceiling fans, and newer windows with screens in all main level roomsbr- Appliances: Dishwasher, refrigerator/freezer, oven with stovetop, washer, dryer, water filtering system, and hot water tankbr- High-speed 2-gig fiber internet connection, satellite TV, and 4G mobile inside and outside on the propertybr- Wood stove (firewood on site)br- Newer wood floors throughoutbr- Garage and plenty of room to store ski, snowboard, or outdoor equipmentbr- Full basement with radiant floor heatingbr- Private dock on water during warmer months (put-in typically just prior to Memorial Day weekend; take out typically between end of October and Thanksgiving; exact put-in and take-out dates are vendor- and weather- dependent)br- Canoe and kayaks available for usebr- Full-size pool table, ping pong, air hockey, board games, puzzles, kids toys and morebr- 2+ acres of land

Bed

Bath

Sleeps

$808.42

/ Nightly

Private Vacation Home

Highland Dream: All Season Beauty! 5BR/2BA, Lakefront, Stay and Play. 4 Season

Bridgton, Maine, United States

If you’re looking for the perfect private getaway you found it here. Highland Dream is a 5 bedroom waterfront home featuring a large waterfront area with a unique 40’ private sandy beach, gently sloping sandy swim area, and a large dock and raft. Plenty of space for all your summer fun, be it badminton, cookouts or just sunbathing. Enjoy sunrises over a quiet lake perfect for canoeing, kayaking, paddle boards, or just listening to the loons play. You’ll never forget morning coffee on the point, or nighttime fire pits under the stars. brbrAll about the view, this home features a newly renovated kitchen with a lake view and 2 fully updated bathrooms. The 1 King and 2 Queen bedrooms have lake views through large picture windows, and 2 bunk rooms to accommodate up to 12 comfortably, (not including the fold out couch)..brbrThe quaint town of Bridgton is 1 mile away with shops, antiques, and all your vacation needs. Bridgton has its own Theater (with a pub) for rainy days, and Twin Drive-In theater, only a short drive away. Hannaford foods is a 5 min drive to stock up. brbrAnd come visit in the other seasons as well, with tremendous leaf-peeping and Autumn fun, like the Fryeburg Fair and Apple Picking nearby, amazing snowmobile and skiing within easy distance, along with ice fishing, cross-country skiing, ice-skating, and everything else that is great about winter outdoors! Then come back to sit by the fireplace, have a great meal at home, and catch a game or movie on the big TV. brbrLooking to venture out br-Boat, waverunner and Paddle board rentals nearby br-Take a relaxing canoe trip on the Saco River, only 20 minutes away.br-Old Orchard Beach and other popular ocean beaches are only 1 hour away.br-Shawnee Peak Ski mountain is just 5 miles from your door for tons of family friendly slopes and a terrain park. Several other popular ski areas are within 30-60 minutes.br-Fryeburg Fair in October is a 15 minute drive.br-North Conway is a 30 minute drive with outlet shopping, fine restaurants, and stores galore. br-Historic Portland Maine is about 1 hour away with tons of culture, shopping, food and pubs, and excellent day-long excursions.br-All Trails app will give you plenty of hiking options close by.br-Golfing at Bridgton Highlands is on the other side of the lake just 5 minutes away, and the highly acclaimed Point Sebago Resort and Golf is just 20 minutes awaybrbrThere's so much to do here that we can't possibly explain it all, but drop us a line and we'll be happy to help you find the perfect way to spend your time in Bridgton, Maine.

Bed

Bath

Sleeps

$324.78

/ Nightly

Private Vacation Home

New home in the lakes region. 1/ mile to Pleasant Moutain

Bridgton, Maine, United States

2 yo old home in Knights HIll Association. Access to pool (till Sept 15), lake front beach and bathrooms. Perfefct location for antique shopping, golfing weekend, girls weekend away, foliage trips, Frybeurg Fair (10 miles away, Sptember 2-October 5)

Bed

Bath

Sleeps

$356.0

/ Nightly

Private Vacation Home

Lake Front Cabin on Desirable Highland Lake

Bridgton, Maine, United States

Escape to this lakefront cabin in Bridgton, Maine—your four-season retreat.brbrSummer: Live the lake life! Enjoy our 15 ft private sandy beach, swim in the crystal-clear water, and use our canoe and kayak for sunset paddles.brbrFall: This is the time for cozy relaxation. Take in stunning foliage views, go hiking or apple picking, and end the day gathered around the fire pit.brbrWinter: Experience a snow-filled wonderland. Ski, snowshoe, or cross-country ski, then come home to a warm, inviting cabin.

Bed

Bath

Sleeps

$301.57

/ Nightly

Private Vacation Home

Cozy home in Bridgton Maine!

Bridgton, Maine, United States

Lake access to beautiful Highland Lake in a quiet neighborhood walking distance to the association beach! In the summer enjoy swimming, fishing, kayaking, hiking and more! Golf at Bridgton Highlands Country club or other courses nearby! Come see the beautiful fall foliage and walk or hike our local trails or take a drive to the White Mountains! Pleasant Mountain is a few miles away to downhill ski in the winter! Sunday River is approx. a 40 min drive for more skiing fun! Five Fields Farm in Bridgton has cross country skiing, snow shoeing and apple picking! Snow mobile trails are nearby and are easily accessible when the lake is frozen. Bridgton center has wonderful restaurants, shopping, antique stores a movie theatre and a drive -in when the weather is warm! North Conway, NH is 30 min away with more restaurants and shopping. br Our home is the perfect way to end the day and relax. We have an outside fire pit, gas fireplace for colder nights and air conditioning for hot summer nights. A wrap around deck for morning coffee or a barbecue dinner outside. Come visit Bridgton and the Lakes region in Maine any season and enjoy all we have to offer!

Bed

Bath

Sleeps

$3034.17

/ Nightly

Private Vacation Home

Fabulous Waters Edge with Sandy exclusive beach

Bridgton, Maine, United States

To View a 3D Tour: https://my.matterport.com/show/ m=B5UnAeCTcEp&brand=0&mls=1&brbrbrNestled on the scenic shore of Long Lake with no walk to the beach (your own private beach), our expansive private estate provides a tranquil and comfortable retreat only steps from the water and sandy beach. This luxurious lake house is tucked within the beautifully manicured yard and features its own sandy beach, offering a shallow entry point that is welcoming for anyone. The beach is easily observable from the comfort of the house, three decks, or while lounging in the yard.brbrThe home itself spans three levels and has ten bedrooms, six bathrooms, and three separate living areas, creating ample space for relaxation and socializing. Each viewpoint from the front and sides of the residence presents uninterrupted views of Long Lake, ensuring that every moment of your stay is accompanied by a breathtaking backdrop.brbrThe kitchen is fully equipped with all the necessities for your cooking and entertainment needs, including a selection of board games for cozy nights. Comfort is further enhanced with the provided beach towels and the convenience of having a washer and dryer on the premises. To ensure an enjoyable and active stay, you'll find table tennis, a wifi enabled television for downtime, paddleboards, a fire pit (with wood supplied for your use), corn hole, inviting Adirondack chairs enhanced with outdoor lighting, and kayaks.brbrSleeping Configurationbr- Top Floor: The primary suite features a king-sized bed, a futon, and a private en suite. Additional top-floor accommodations include rooms with a king bed, queen bed, and futon arrangement. (Three rooms, One with a king-size bed and futon, one with a queen bed and futon, and one with a queen bed)brbr- Main Floor: Offers a wheelchair-accessible room furnished with a queen bed, alongside another room featuring two full-sized beds. ( 2 bedrooms, one with a queen size bed, one with two full-size beds and a futon)brbr- Bottom Floor: This level provides direct access to the yard and beach and includes rooms with a combination of full and twin beds, two bunk beds, and two additional full-sized bedrooms. (five rooms, one with two full-sized beds, one with a queen-size bed and twin-sized bed, one with a queen-size bed, one with two sets of bunk beds, one with a king-size bed)brbrbrLocal Attractionsbr- Skiing: Winter sports enthusiasts can hit the slopes at Shawnee Peak and North Conway, both located within a short driving distance, offering challenging trails and breathtaking views for a thrilling downhill experience. Alongside skiing, the Sunday River area offers opportunities for snowmobiling on well-groomed trails, providing an exciting way to explore the scenic terrain. Ice fishing is also a popular activity, where you can relax on the frozen lakes and try your luck at catching fish in a serene winter setting. (Shawnee Peak Distance: 18 Minutes | North Conway Distance: 42 Minutes | Sunday River: 55 Minutes) brbr- Sunspots Lessons: your ultimate destination for wakeboarding, water skiing, wake surfing, and paddleboarding, where expert guidance and top-of-the-line gear promise an unforgettable adventure on the water. (Distance: 15 Minutes)brbr- Long Lake Marina: offers an extensive selection of boat rentals, top-notch services, and repairs, ensuring an outstanding boating experience for all marine enthusiasts. (Distance: 15 Minutes)brbr- Golfing and Tennis: Enjoy an unbeatable golf and tennis experience at Bridgton Highlands, a scenic and friendly open-to-the-public facility nestled in Maine's Lakes Region. The facility offers stunning views, a range of activities, and a welcoming atmosphere for all ages and skill levels. (Distance: 14 Minutes)brbr- Portland, Maine: A charming blend of historic architecture, renowned seafood eateries, vibrant arts scene, and picturesque waterfront, all converging to create a unique coastal city experience. (Distance: 1 Hour)brbr- Songo Locks: Discover the enchanting Songo Locks, a historic waterway offering picturesque views and a serene spot for boating. (Distance: 24 Minutes)brbr- Dining and Shopping: A 5-minute drive takes you to Bridgton Town Center for dining at venues like Venezia Ristorante and Black Horse Tavern and eclectic shopping at Renys, while the renowned North Conway outlets are just a scenic drive away, offering a variety of shopping experiences. There are also numerous boat docks you can pull up to along the lake with American comfort food. (North Conway Distance: 42 Minutes)brbr- Grocery Shopping: The Hanaford supermarket will satisfy all your food and supply needs during your stay. (Distance: 9 Minutes)brbrOur home has a large dock encouraging you to swim, fish, or sail on Long Lake's pristine waters. Moreover, you'll have access to a vast network of waterways as Long Lake connects to Brandy Pond and Sebago Lake, offering over 60 miles of boating adventure.brbrEmbrace the ultimate lakeside living experience where sophistication meets the raw beauty of Maine's natural landscape. Your unforgettable retreat awaits a harmonious blend of privacy, luxury, and unspoiled waterfront access.brbrFAQbrDo we host weddings or events brWe have made the difficult decision not to permit wedding parties or events at our property. After careful consideration, we concluded that the associated liability and increased wear and tear on the premises necessitate this policy. We appreciate your understanding and cooperation in respecting this guideline.brbrBedroom Configurations:brOur property features a diverse assortment of 10 well-appointed bedrooms to accommodate a variety of guests comfortably:brbr2 Bedrooms, each with two Full-size bedsbr1 Bedroom with two Queen-size bedsbr2 Bedrooms, each with a single King-size bed (one of these rooms also includes a Queen-size futon)br1 Bedroom with a single Queen-size bedbr2 Bedrooms, each with a single Full-size bedbr1 Bedroom with four Twin-size bunk beds (ideal for younger guests or singles)br1 Bedroom with a Full-size bed and a Twin-size bedbrbrbrIs parking available on the property brOur property boasts plentiful parking options. Easily accommodating 10 vehicles or more.brbrAre pets allowed on the property brPets are permitted, although certain fees may apply. Prior notification is necessary. You will be directly billed for any damages caused by your pet. We kindly request you ensure property maintenance and care by cleaning up after your pet.

10

Bed

6

Bath

25

Sleeps

$327.0

/ Nightly

Private Vacation Home

Peaceful family cabin in the woods

Bridgton, Maine, United States

Experience the magic of the Maine woods in our family cabin. Stay comfortably in Bridgton at this 3-bedroom house. With 1 king bed, 1 queen bed, and 2 twin beds with trundles in the loft, guests will find a peaceful retreat. The house features 2 full bathrooms. The back yard is spacious and great for playing outdoor games or take a walk through our mini enchanted garden. brLocated 15 minutes away from Pleasant Mountain where you can enjoy skiing or hiking. We are just under 5 miles from Highland Lake as well. Enjoy the shopping in North Conway, NH or in town. Plenty of local places to eat/drink. We hope you enjoy your stay with us!

3

Bed

2

Bath

8

Sleeps

$1100.13

/ Nightly

Private Vacation Home

Tranquil bungalow with WiFi in charming Bridgton

Bridgton, Maine, United States

Enjoy a soothing stay at this 2-bedroom bungalow in Bridgton. The bedrooms feature 1 full bed and 1 twin bed, perfect for a small group of guests. The bathroom comes equipped with a bathtub and a hairdryer for your convenience. Experience what Bridgton has to offer with a stay at our bungalow.

Bed

Bath

Sleeps

$276.39

/ Nightly

Private Vacation Home

Discover the Perfect Maine Escape on Long Lake, Bridgton. The Way Life Should Be

Bridgton, Maine, United States

Nestled among the trees on beautiful Long Lake, this recently renovated cabin offers the very best of Maine living in Bridgton—“the place for all seasons.” Enjoy peaceful mornings overlooking the beach and dock, with the soothing sound of Stevens Brook cascading over the rocks and the distant call of loons. Just 250 feet away, a private beach (shared with one other home) invites you to swim, boat, or simply relax by the water.brThe cabin comfortably sleeps guests in three bedrooms: a primary suite with a queen bed and private bath, a bunk room with two bunks and full-size futons, and a third bedroom with full-size beds. With ample closet space, a fully stocked spacious kitchen, and the convenience of a washer and dryer, you’ll have all the comforts of home.brClose to Bridgton Center, North Conway, and Freeport for shopping and dining, this lakeside retreat is the perfect place to unwind and enjoy Maine before the summer crowds arrive.

Bed

Bath

Sleeps

$205.9

/ Nightly

Private Vacation Home

Ell Suite walk to town beach

Bridgton, Maine, United States

The Ell Suite, nestled between the manor, and attached barn at The Fowler House. This charming unit has a cozy cottage feel, full kitchen, and newly renovated bath. Just steps away from downtown historic Bridgton and its many restaurants, pubs, shops, and galleries. Within walking distance to several parks, and the lovely Highland Lake beach, boat launch. Only a 5 minute drive for skiing at Pleasant Mountain Ski Area, 35 mins. to No. Conway, Nh., and 1 hour to Portland .-located place.brbrDirectly In town, The Fowler house is walking distance to the Beach, restaurants, shops and other attractions as well as convientky located to nearby attractions. brbr.Shared outdoor space if the other 1 bedroom suite in the Fowler House is rented.

Bed

Bath

Sleeps

$328.58

/ Nightly

Private Vacation Home

New for 2026! Moose Pond Retreat with Private Waterfront & Fun Activities

Bridgton, Maine, United States

Discover the tranquility of Moose Pond’s northern end at this welcoming lakeside retreat. Spend your days on the pond with the provided canoe, paddleboard, or four kayaks (2 adult, 2 youth), and enjoy your private waterfront and dock. In the evenings, gather around the lakeside firepit to toast s’mores and take in the starry night sky.brbrThis cozy home comfortably accommodates up to six guests with three bedrooms and two full bathrooms. Beyond the private waterfront, you’ll have access to the Knight’s Hill Association amenities, including a beach, pool, tennis court, and basketball court—perfect for fun-filled family days.brbrJust a short drive from Pleasant Mountain, the property is ideal for a winter ski getaway, while the lake and outdoor activities make it a wonderful summer retreat. Whether you’re seeking water adventures, relaxing evenings by the fire, or seasonal recreation nearby, this home is a year-round escape for families and friends.brbr2026 Rates: $300/night PEAK season; $275/night LOW/OFF seasonbr** NOW ON SPECIAL: $275/night PEAK season; $250/night SKI season; $225/night LOW/OFF seasonbrbr* Sheets, pillowcases, beach towels, and bath towels not provided *brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

3

Bed

2

Bath

6

Sleeps

$308.83

/ Nightly

Private Vacation Home

Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!

Bridgton, Maine, United States

brCome stay and play at The Bear’s Den in West Bridgton, Maine! brbrNestled snuggly in the woods of the Knights Hill Association, this home is situated on a wooded half-acre lot. Featuring 3 bedrooms and 2 bathrooms, it can comfortably accommodate up to 10 guests. (We also have an additional two cots with sleeping bags, and two pack and plays with mattresses and bedding for them, as well.) brFrom its rough-hewn boards to its modern kitchen, this home is an absolute delight. Our previous guests have described it as feeling like they were in a tree house, while others have said they feel as if the house welcomed them with a warm hug. There is something very special about The Bear’s Den and the location is perfect for experiencing all the wonderful amenities from the Lakes Region of Maine to the White Mountains of New Hampshire! brWe have an automatic whole house generator, so you will never be without power and hot water should there ever be a power outage. The hot water is also on demand. That means that dishwasher can be running, while both bathrooms are in use (including the jetted tub), even if there is a load of laundry in the washer. Perfect after a fun day on the slopes, hiking, or a day at the beach!brWe are a pet friendly home. We welcome up to two well-behaved dogs to accompany you during your stay. A friendly reminder that Bridgton has a leash law, and that the association does not allow pets on the beach or around the pool area.brThe Knights Hill Association Moose Pond beach, playground, and clubhouse are just down the street. Less than a 10-minute walk or 2-minute car ride. We have two kayaks available at the beach for your use during the summer months. The outdoor association pool, clubhouse, playground, and tennis, pickleball, and basketball courts are located across the street and available for use in the warmer months, too. They are also less than a 10-minute walk or 2-minute car ride.brHop in your car and you are only 5 minutes from the base of Pleasant Mountain. Hiking and biking in the warmer months and skiing and snowboarding in the winter months. There are also plenty of places to snowshoe, cross-country ski, and (ice) fish, around the Moose Pond area. Warm up at the end of the day with a meal or s’mores around the firepit, soak in the jetted tub in the main floor bathroom, and/ or curl up on the downstairs couch in front of the gas fireplace. brWhatever your pleasure, The Bear’s Den is a delightful four-season retreat! We can’t wait for you to book your stay with us and see for yourself!brbrFYI-The Bear's Den calendar tends to fill rather quickly. If your requested dates are not available, please reach out to us. We can add you to our wait list so you will be one of the first to know if there is a guest cancellation. Thank you!

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$367.88

/ Nightly

Private Vacation Home

Lakefront Paradise on Northern Tip of Long Lake

Bridgton, Maine, United States

Quiet, Private house with great lakefront, modern style and one of the premier locations on the lakebrNewly renovated main house, plus separate detached apartment sleeps up to 6 adults, or 4 adults, 2-4 kids comfortablybrProperty is steps from the lakefront, and has its own sandy pier/beach for afternoon sunbathing and swimming or cocktail hour. 2 docks, plus a mooring allow easy boat access during your stay. brFishing in this cove either from the dock or your boat are among the best on the lake.brbrThis is the perfect landing spot for a family vacation, get together with friends or late summer getaway.

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$882.9

/ Nightly

Private Vacation Home

Luxury Lakefront Living in Lake Sebago Area

Bridgton, Maine, United States

25 Years New Quality Custom 5 bedroom Lakeside Rabbit Ear Colonial. Pool table, 3 fireplaces & recreation and kitchen bonus area in beautiful finished daylight basement, two deck levels.. All the comforts of home (cable & internet) plus outside hot tub! WOW. But don't forget the reason you came 242 feet of PRIVATE long lake frontage dock and float!! This is simple a great place winter and summer.

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$147.92

/ Nightly

Private Vacation Home

Bear Trap - A Magical Place in all Seasons

Bridgton, Maine, United States

Bear Trap Road is a private, gated community with awesome mountain views. Our house is a seven gable home with an open kitchen, dining, and living room area, three bedrooms, and 2.5 baths. Because our property sits high, there is a steep drop off that is not suitable for young children. If being secluded, but not more than 10 minutes from town is your idea of tranquility, this is the place for you.

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$335.72

/ Nightly

Private Vacation Home

Cozy Library Tiny Home *Private Hot Tub* King Bed *Minutes to Lakes & Hiking

Bridgton, Maine, United States

Welcome to Maine's most unique tiny home! This antique library building has been newly renovated into a cozy getaway for bibliophiles and library lovers alike. Its book-lined shelves and dark academia decor, along with modern amenities and high quality bedding ensure a memorable stay, while the gas fireplace and hot tub provide the perfect ambiance for rest and relaxation. Whether you're a bookworm or just in need of a quiet escape, The Tiny Library is the perfect retreat.brbrOVERVIEW brOpened in 1928 as the Perley Memorial Library and Reading Room, this unique tiny home has been lovingly restored and named The Tiny Library. The original 380 square foot building now contains a book-filled sleeping loft with a comfy king and twin bed. Warm wood tones and the dark and moody decor make for a luxurious atmosphere. The original bead board walls and ceiling plus three original bookcases help to preserve the library character. These elements were built upon to create this truly memorable vacation rental.brbrThe property is a peaceful combination of fields and woods in a quiet, private setting. The outdoor space allows for grilling, roasting s'mores over the seasonal fire pit or relaxing in the 4 person year-round hot tub while looking at the stars after a day of swimming, hiking, shopping or skiing. brbrBEDROOMbrThe sleeping loft is the only bedroom and is up a steep alternate tread staircase. There you will find a comfortable king bed with a memory foam mattress, ultra soft cotton sheets and a fluffy duvet. There is also a twin XL bed in a cute and cozy corner of the room.brbrBATHROOMbrThe bathroom is tiny but the shower is nice and roomy. Everything you need is provided from body wash, shampoo and conditioner to bath and hot tub towels to extra toilet paper and a hair dryer.brbrKITCHENbrThe kitchen is small (notice the theme here ) but comfortable to work in with its propane cooktop, large sink and gorgeous stone countertops. It is well stocked with cookware, bakeware, dishes and utensils as well as a toaster, toaster oven, microwave, some spices and cooking spray and oil. brbrWe built a coffee and tea bar with the coffee lover in mind! Drip and French press coffee can be made to allow you to enjoy the perfect cup your way. A variety of tea is provided as well as regular and decaf coffee beans for grinding. While we provide enough to get you going for a few days, longer stays may require a trip to the grocery store to replenish the supplies. brbr**The library has a wonderful curated selection of hundreds of books! Please feel free to check out a book (permanently!) if you find one you'd like to continue reading after your stay with us. We only ask that you take out fiction books and leave the nonfiction for others to enjoy during their stay.**brbrTHE OUTDOOR AREA brbrRight outside the back door you'll find the roomy hot tub in a private setting with rock walls and woods as the backdrop. The hot tub can be enjoyed in rain with it's new pergola. The side yard is where you'll find the fire pit. We do not supply firewood as a rule, but there may be some left behind from others and may get you started on your first night. Dry fire wood bundles can be bought at the Irving station about 6 minutes away or at the Hannaford grocery store about 8 minutes away and are generally about $8. brbr**Please note that The Tiny Library is located about 100 feet from our Schoolhouse Retreat which is also a short term rental. There is a privacy fence between. The long part of our pull through driveway is shared by the two buildings, but they each have their own parking areas. The Schoolhouse and Library do not share any amenities. We rent the two properties separately, but also have a listing for the two buildings to be rented together for a larger group.** brbrGuests will have access to the Library and the surrounding yard from the fence to the right. Please keep in mind that this is Maine and there is wildlife in our area including ticks. brbrWhile I won't be available in person I do live nearby and am available to answer questions!brbrI am only a call or text away to answer questions!brbrThe Tiny Library is located near many of the area's best attractions including:brbrDowntown Bridgton - 9 minbrNaples Causeway - 10 minbrPleasant Mountain Ski Resort - 16 minute drivebrSebago Lake State Park - 16 minbrNorth Conway - 42 minbrPortland, Maine - 1 hrbrSunday River Ski Resort - 1 hrbrBoston - 2.5 hrsbrbrThere are many wonderful restaurants close by in Bridgton and Naples. The closest restaurant, Campfire Grill (nothing fancy but so good!), is a 6 minute drive. The library is also in the middle of many lakes and ponds including Long Lake, Sebago Lake, Moose Pond and Highland Lake with many places to swim, minutes from great hiking trails, the twin drive-in and a movie theater as well as shopping and all the White Mountains and North Conway have to offer.brbrThere is a parking area for 2 vehicles in front of the library. In the snowy season, we do our best to ensure the driveway and parking areas stay cleared but winter in Maine is unpredictable and there are times when we have to wait our turn to be plowed or shoveled out. Please reach out if there is any issue with snow and we will send someone as soon as possible.brbrThe stairs to the loft are steep and have alternating treads for comfort and ease of climbing.brbrRental contract required for every booking! To be sent to guest upon booking with the 48 hour zero penalty cancellation period. brbr***We require all guests (unless children accompanied by a parent) be at least 21 years old.***brbrThe Tiny Library is perfect for couple or a small group of friends to relax and enjoy vacation together. It won't be the right place for you if you are interested in having an all day and night drinking fest. brbr*****Sorry, no pets, no parties or events and no smoking or vaping of any kind ($300 fine).****** brbrMaine is home to ticks, mosquitoes, black flies, ladybugs, stinkbugs, spiders, deer, turkeys, bats, racoon, skunks, bees and more! While our housekeepers and pest control service work hard to keep things very clean and tidy, the reality is we are a 100+ year old building in the country in the mountains of Maine - so you may encounter some wildlife! brbrPlease note that while we have a quiet 7+ acre property, the library is located in a small rural Maine neighborhood with homes of all types and ALL conditions. There are a couple neighbors you can partially see through the woods and occasionally cars drive by. If your group does not also rent the Schoolhouse Retreat next door, there will likely be guests there during your stay. It shares the property but does NOT share amenities. The Schoolhouse is about 100 ft away from the library with a 6 foot tall privacy fence between.brbrThere are a few things we ask guests to do for checkout - brbr-load and start the dishwasher brbr-close any open windows, turn off lights and lock doors brbr-any full trash bags can be placed in the bin outside by the fence

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3

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