Vacation Rentals By Owner In Rockland, ME

$405.14

Oceanfront -Samoset Road, Rockland ME (Across from the Samoset Resort)

Rockland, Maine, United States

This Vacation home is located across the street from the famous Samoset Resort. It is walking distance and on the same street as the Rockland Breakwater Lighthouse. Area Attractions include Camden Hills State Park, Farnsworth Art Museum, Less than 10 minutes to Downtown Camden, Samoset Resort, Wyeth Center, Owl's Head Transportation Museum, Owl's Head Lighthouse & minutes from Ferry's to Vinlhaven and Northhaven. Area Events include Downeast Jazz Festival, North Atlantic Blues Festival, Friendship Sloop Days, Rockland Lobster Festival, Maine Homes & Harbors Show and many more.brbrRockland Short Term Rental Permit # STR23-35br

3

Bed

2

Bath

6

Sleeps

$336.08

/ Nightly

Apartment

Cozy Carriage House with Rockland Harbor View

Rockland, Maine, United States

Cozy garage studio apartment and fenced in yard. Rockland Harbor unobstructed View. Next to a park, boardwalk and beach. Easy walk to downtown. Hardwood Floors, vaulted ceilings. Brand new renovation.

1

Bath

2

Sleeps

Exceptional(6)

$603.54

/ Nightly

Condo

Rockland Central Over Main, downtown living

Rockland, Maine, United States

Apartment on Main Street; Walk to Shops, Restaurants & Harbor brExperience the ultimate vacation in this enchanting apartment, perfectly located just steps from the best local restaurants , boutique shops, and fascinating museums. Situated right on Main Street, you'll be in the heart of the action with the charm of a nearby park for relaxing strolls or the excitement of nearby day trips. brbrFor a serene escape explore the picturesque fishing villages, marinas, and fishing charters just a short distance away, offering the ideal setting for a tranquil day on the water. When it's time to unwind retreat to the apartment's bright and spacious living area. With its elegant flooring and homely comforts you'll feel right at home. Enjoy your favorite movie or TV show on the flat-screen TV or cook up a storm in the fully equipped kitchen perfect for preparing delicious meals. brbrFeeling indecisive about where to dine The neighborhood boasts an impressive selection of restaurants within walking distance so you're never far from a great meal. This apartment offers an unbeatable combination of prime location and cozy inviting ambiance making it the perfect choice for your next getaway. brbrBook now to start making unforgettable memories. With complimentary WiFi you can easily plan your adventures or share your vacation highlights with friends and family. Please note that the apartment is situated on the third floor of a four-story building accessible by stairs. brbrBe aware that Main Street may be closed during some annual events. To avoid any disruptions check in before 5 PM on these special event days. Notable events include: - Summer Solstice - North Atlantic Blues Festival - Annual Lobster Festival - Parade of Lights (featuring the lighting of the Lobster Trap Holiday Tree)brbrFor more information or if you have any questions don't hesitate to reach out. We look forward to hosting you!brbr*Security Camera in front lobby.

2

Bed

1

Bath

4

Sleeps

$359.62

/ Nightly

Private Vacation Home

Dog-friendly historical home with recent updates, porch & prime in-town location

Rockland, Maine, United States

Find 19th-century charm and every modern convenience at this ideally located family home in Rockland, where you'll be a matter of steps from downtown's wonderful restaurants, shops, and scenic harbor.brbrIdeal for a long-term stay (30-night minimum), this two-story home sits on a quiet street in downtown Rockland, only three blocks from the historic center. There's so much to enjoy here, with several art galleries, renowned museums, the Maine Lobster Festival, and the Rockland Breakwater Lighthouse all right in town. As the center of Midcoast Maine, Rockland is also an excellent home base for day trips, whether you venture to the picturesque harbors of Rockport and Camden (seven miles), board a boat from Port Clyde to Monhegan Island (17 miles), dine out in Portland (78 miles), or escape into nature in Acadia National Park (80 miles).brbrYou will love spending time on the gorgeous porch and the house features a fenced in yard.brbrThis Queen Anne home dates back to 1896, but it has been thoughtfully updated in the years since with high-speed WiFi, TVs with cable and streaming capability, a washer/dryer, and other contemporary comforts. An en suite bath was added to the renovated primary suite in spring 2024; the newly added stainless steel oven and refrigerator update both the look and functionality of the kitchen. Still, the house also maintains much of its original character, including a wide, shaded porch out front where you can sip your morning coffee in rocking chairs and watch your kids play in the fenced yard. brbrStep inside to be greeted by a living room with a fireplace, a separate family room where you can watch TV in the evenings, and a study with both a sofa bed and a desk to serve as either a home office or a sleeping space. Enjoy an eat-in country kitchen, a gas grill on the porch to sear seafood fresh from the ocean, and ample space for family meals and after-dinner board games at the kitchen and dining room tables. brbrThings to Know

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$466.16

/ Nightly

Apartment

Rockland Central Loft, heart of downtown

Rockland, Maine, United States

Downtown Rockland Apartment Near Restaurants, Shops & Harbor brExperience the ultimate vacation in this charming apartment just steps away from all the best restaurants, shops, and museums. Enjoy the convenience of being right on Main Street where you can take a leisurely stroll through the park or embark on an exciting day trip. brbrLooking for a peaceful day on the water Take advantage of the nearby fishing villages marinas and fishing charters for a relaxing day amidst beautiful scenery. And when you're ready to unwind retreat to the spacious and bright living area of the apartment complete with beautiful floors and all the comforts of home. Watch your favorite movie or show on the TV and then head into the kitchen to whip up a tasty meal. brbrCan't decide what to eat No problem – there are plenty of restaurants within walking distance of the property. Don't miss out on this unbeatable location and cozy accommodation for your next getaway. Book now and get ready to make unforgettable memories. And with WiFi included it's easy to plan your next outdoor adventure or share your pictures on social media. brbrPlease note that this apartment is located on the second floor of a four-story building accessible by stairs. Additionally there are a few annual events throughout the year that may close Main Street so be sure to check in before 5 PM on those days. Don't hesitate to inquire for more information. Some of these events include: - Summer Solstice - North Atlantic Blues Festival - Annual Lobster Festival - Parade of Lights (featuring the lighting of the Lobster Trap Holiday Tree).brbr*Security Camera in front entrance.

Bed

Bath

Sleeps

$255.06

/ Nightly

Apartment

Elegant 2-Bedroom Apartment in Historic 1862 Sea Captain's House. Pets welcome.

Rockland, Maine, United States

Elegant Ground Floor Apartment in Historic 1862 Sea Captain's House. Revel in English and American period antiques and original works of art, oil paintings, watercolors and prints. Dine off fine English china. Relish beautiful French fabric curtains and handmade quilts. brbrLovingly restored and renovated to exacting standards, the house retains its original features, wood floors and gracious moldings. brbrMaster bedroom with double bed, en-suite bathroom, TV. Second bedroom with two twin beds. Both bedrooms air-conditioned. Clean fresh linens and comforter covers.brbrMain bathroom with shower over tub. En-suite bathroom with shower. Both provided with plentiful towels and wash cloths. Shower gel, shampoo and conditioner supplied.brbrStately Dining Room, with period English furniture and polished oak table and chairs.brbrCharming and cosy Living Room with comfortable armchairs, sofa-bed and TV. Wood stove, firewood provided.brbrSpacious eat-in Kitchen with period English table and chairs. Excellent appliances, including dishwasher & washer-dryer. Coffee maker, toaster, microwave, stove, full complement of pots, pans and cookware. brbrDesk area adjacent to kitchen. High-speed internet and wi-fi throughout house. brbrLarge deck with table, chairs and umbrella. Charcoal BBQ (charcoal supplied). Fire pit, chairs and picnic table in garden. Firewood supplied.brbrPrivate entrances. Ample parking. Minutes from historic main street. The Captain Zadoc F. Brewster House is perfectly located to explore the Rockland & Camden Area, Penobscot Bay, Maine Lighthouses & Islands, and Acadia National Park.brbrLocal Attractions: Visit the outstanding Farnsworth Art Museum or the world famous Owls Head Transportation Museum. Stroll through Rockland's art gallery district - fifteen galleries in all. Walk out on Rockland Breakwater to visit the lighthouse. brbrDrive to Owls Head, Marshall Point and Pemaquid Lighthouses. Drive to Camden and Rockport, beautiful towns and lovely harbors. brbrDrive up or climb Mount Battie for spectacular views over Penobscot Bay. brbrTake a ferry to Vinalhaven, North Haven, Isleboro or Monhegan and experience island life. Enjoy an evening out at one of Rockland's wonderful restaurants, pubs and wine bars.brbrSpring, Summer and Fall Activities: Whatever the season, whatever the sport, there's something for you here in the Rockland area. Stroll, walk, run, or hike. Rent a bike or a kayak. Take a windjammer cruise. Go deep sea fishing. Go rock climbing at Camden Hills State Park. Golf at 'one of the 75 best golf courses in the country', or at two other public courses. brbrExplore the fascinating communities on the numerous peninsulas nearby and inland. Fall foliage is spectacular. brbrWinter Activities: Cross country ski on local trails or down hill ski nearby at Camden Snow Bowl. Or take the worthwhile trip to the famous Sugarloaf Mountain area. Tobaggan or watch the World Tobaggan Championships at Camden Bowl. Ice climb in the Camden Hills. Ice boat on the frozen lakes. Or cook up a storm in our lovely kitchen and settle by a roaring fire to read or watch TV.

2

Bed

2

Bath

6

Sleeps

$466.9

/ Nightly

Apartment

Kimball Apartment, Modern Studio on Main Street Ro

Rockland, Maine, United States

Downtown Rockland Studio with Historic Charm; well-appointed brStay in the heart of Rockland's vibrant downtown in this fully renovated one-bedroom studio, perfectly blending modern comfort with timeless character. Built in 1853, the original brick building has been carefully preserved with historic details intact, offering a unique connection to Rockland's storied past. Situated on the quieter back side of Main Street, the apartment provides peace and privacy while keeping you just steps from the energy of downtown.brbrInside, you'll find a queen bed in a thoughtfully designed studio layout, a modern and convenient bathroom, and a cozy living space filled with natural light. The convenient-sized kitchen is fully equipped with essential appliances, ideal for everything from morning coffee to home-cooked meals. A combo washer/dryer adds ease for longer stays, and a wall-hung mini split ensures year-round comfort with both heating and air conditioning. Large windows offer glimpses of the harbor and the bustling Vinalhaven Ferry Terminal.brbrStep outside and down to Main Street, where dining, shopping, and culture await. Enjoy fresh seafood at Ada's, local goods at Main Street Market, and endless galleries and boutiques. Rockland is proudly recognized as the “Art Capital of Maine” - home to the Farnsworth Art Museum and a thriving arts community. Just down the street, the Rankin Block stands as one of Rockland's most iconic historic landmarks, listed on the National Register of Historic Places.brbrA perfect home base for exploring the Midcoast, this one-bedroom studio combines history, art, and modern amenities for an authentic Rockland experience.brbrThings to know:brOne off-street parking spot is included with rental. The parking is on the backside of the building, walking around the building and up the street is required to access apartment. brThe apartment is on the second floor and require stairs to access, no elevator is available.

Bed

Bath

Sleeps

$386.8

/ Nightly

Private Vacation Home

Located Directly On Rockland Harbor

Rockland, Maine, United States

The rockland harbor house is located directly on rockland harbor. The house 2000 sq ft. And has 3 bedrooms with 1 full baths. The house is located on samoset road just a short walk to the rockland breakwater lighthouse which is located at the end of samoset road. The house is conveniently located close to shopping restaurants and in 1/4 mile to the closest grocery store. Rockland is also the location for the maine lobster festival the first weekend in august..brbrRockland Short Term Rental Permit # STR23-35br

3

Bed

2

Bath

6

Sleeps

$966.49

/ Nightly

Apartment

Rockland Central, downtown walk to everything!

Rockland, Maine, United States

Walk to all the amazing things Rockland has to offer. Located on the second and third floor of a beautifully renovated building these two apartments allow you easy access to many restaurants, museums, shops and more. brbrThe first apartment, Rockland Central Loft is a two bedroom unit with a queen bedroom and a double bedroom with a shared full bathroom. Views of Main St from above. A well equip kitchen with dinning table allows you to cook meals if you so desire. A spacious living room with a smart TV is a great spot to catch up on a little R&R. brbrThe second unit, Rockland Central Over Main, is another two bedroom unit with two queen rooms and a shared full bathroom. A spacious living room and dining area along with a small sitting room that is perfect for peaceful reading. brbrExplore Rockland and near by towns from this luxury apartment on Main St. Each unit has a parking spot.brbr*Security Camera in front lobby.

Bed

Bath

Sleeps

$484.25

/ Nightly

Private Vacation Home

Rockland Home w/ Deck 5 Mins to Historic Downtown!

Rockland, Maine, United States

Built in 1868, this lovely 3-bedroom, 2-bath vacation rental house exudes New England culture and charm in southern Rockland. This updated home accommodates up to 8 travelers and sits within a 5-minute drive to the dynamic shops, restaurants, and museums in historic downtown. Enroll in a sailing lesson, rent a kayak, or visit the Owls Head Lighthouse just 5 miles away. Attend a seasonal event in Harbor Park or take a scenic 20-minute drive up the coast to explore the picturesque town of Camden!brbr-- THE PROPERTY --brbrCity License Number: R18-34 | State License Number: STR19-41 | Nearby Boating | Historical Value | Pet Friendly w/ Fee (1 Pet Max)brbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds | Living Room: Double Pullout BedbrbrHOME FEATURES: Playground, nearby hunting, hiking trail on-sitebrKITCHEN: Fridge, stove/oven, dishwasher, microwave, cooking basics, coffee maker, dishware/flatware, paper towels/trash bags, spicesbrGENERAL: Free WiFi, linens/towels, washer/dryer, central air conditioning, ceiling fans, complimentary toiletries, hair dryer, iron/board, keyless entrybrFAQ: Stairs required, pet fee (paid pre-trip)brPARKING: Driveway (6 vehicles)brbr-- THE LOCATION --brbrYou couldn't ask for a more convenient location in Rockland! Located on Main Street surrounded by mature pine and cedar trees, this home is only a 15-minute drive from Owls Head State Park that features an operational lighthouse with seasonal tours and gift shop. brbrTake a 5-minute drive to downtown where the Center for Maine Contemporary Art, The Maine Lighthouse Museum, and the Mississippi Blues Trail eagerly await to entertain you. Eat with the locals along Main Street at venues such as the Rock City Cafe, Rustica, or Park Street Grille. brbrIf you're in town for the Lobster Festival - you won't have to travel far to experience the fun at Harbor Park! This event venue is only a 12-minute walk away, so be sure to check the calendar for other seasonal events. brbrIf you're itching to drive up the coast, visit Camden just 20 minutes north. Admire the early 19th-century architecture before kayaking in Penobscot Bay. View the scenic terrain from one of the trails in Camden Hills State Park after touring the restored Opera House with family and friends!brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $150 fee (+ fees & taxes, 1 pet max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to access

Bed

Bath

Sleeps

$147.48

/ Nightly

Private Vacation Home

1/2 Mi to Dtwn & Harbor Park: Home w/ Large Yard!

Rockland, Maine, United States

Pet Friendly w/ Fee | Roku + Netflix | Near Waterfront Dining | 4 Mi to Pen Bay Medical CenterbrbrNestled in the heart of Rockland, with easy access to restaurants, shops, parks, and hospitals, this 3-bedroom, 2.5-bath vacation rental is ideal for travel nurses and those seeking long-term accommodations. Explore the waters of Penobscot Bay, visit the Rockland Breakwater Lighthouse, or attend the Maine Lobster Festival. Afterward, gather back at the house for a home-cooked meal and a movie night!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 full bedbr- Bedroom 3: 2 twin bedsbrbrMAIN FEATURESbr- Smart TV w/ Roku & Netflixbr- Spacious fenced yardbr- 4-person dining tablebrbrKITCHENbr- Refrigerator, dishwasher, stove/oven, microwavebr- Keurig coffee makerbr- Cooking basicsbrbrGENERAL br- Free WiFibr- Central A/C & heatbr- Linens/towels, complimentary toiletriesbrbrFAQbr- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- Multi-level home, 4 steps for entrybr- Small interior steps for full accessbr- Bedroom & full bath on 1st floorbrbrPARKINGbr- Driveway (2 vehicles)br- Free street parking (first-come, first-served)brbr-- THE LOCATION --brbr- Close to local conveniences & seafood marketsbr- Half-mile to Farnsworth Art Museumbr- 3 miles to Rockland Breakwater Lighthousebr- 5 miles to Owls Head State Parkbr- 10 miles to Camden Snow Bowlbr- 67 miles to Bangor Int’l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This multi-level home requires 4 steps to enter and small interior steps for full access; there is a bedroom and full bath on the 1st floor

3

Bed

2

Bath

6

Sleeps

$95.92

/ Nightly

Cottage

Coastal Rockland Summer Retreat – Waterfront View

Rockland, Maine, United States

Charming coastal home in Rockland’s south end, available summer 2026 from May through October. brbrWelcome to 3 Trinity Street, a cozy Rockland retreat in a quiet neighborhood just minutes from the harbor, restaurants, galleries, and festivals. Whether you are here to explore Midcoast Maine, work remotely, or enjoy a long seaside vacation, this property gives you a comfortable home base with easy access to everything in town.brbrInside, you’ll find a bright, well‑kept space with comfortable seating, a functional kitchen, and inviting bedroom ready for longer stays. The layout works well for a couple, small family, or solo traveler who wants more space and privacy than a hotel can offer. Ample natural light and simple coastal touches make the home feel relaxed and welcoming.brbrStep outside and you’re a short walk or quick drive from Rockland’s working waterfront, ferry terminal, Main Street shops, and local dining. Day trips to Camden, Rockport, Owls Head, and nearby beaches are easy, and you’ll be close to summer events like the Maine Lobster Festival and North Atlantic Blues Festival.brbrThis listing is designed for monthly guests who want to settle in, unpack, and truly experience life in Rockland for more than just a long weekend.brbrAmenities IncludebrbrFully equipped kitchen (stove, oven, fridge, microwave, basic cookware and dishes)brbrOn‑site laundry brbrOff‑street parkingbrbrBedding and towels providedbrbrWalkable access to harbor, restaurants, shops, and festivalsbrbrRates and availabilitybrAvailability: May 1 – October 31 (summer rental season only)brbrMinimum stay: 1 month

1

Bed

1

Bath

3

Sleeps

$661.46

/ Nightly

Apartment

3 bedroom 2.5 bath apartment with views of Rocklan

Rockland, Maine, United States

STR#- STR25-7brbr3 Bedrooms | 2.5 Bathrooms | Downtown RocklandbrbrWith in walking distance to the waterfront in downtown Rockland, Windows on the Sea is a bright and welcoming second- and third-floor apartment offering beautiful harbor views and an unbeatable location. Just minutes from shops, restaurants, galleries, and museums, this home is an ideal base for exploring Maine's Midcoast.brbrThe apartment features a full kitchen and comfortable living spaces across two levels. The main living level (second floor) includes a queen bedroom with a half-bath ensuite, plus a shared full bathroom. Upstairs on the third floor, you'll find a king bedroom a pass-through to the twin room—perfect for families—along with a shared full bathroom.brbrThe owners reside in the first-floor unit and share the property with their friendly dog, adding a warm, local touch to your stay. Whether you're here for coastal views, culture, or cuisine, Windows on the Sea offers comfort and convenience in the heart of Rockland. brbrA well-behaved dog is allowed with pre-approval. The owner has a friendly dog on premise as well.

Bed

Bath

Sleeps

$463.81

/ Nightly

Cottage

WATERSIDE RETREAT - City of Rockland

Rockland, Maine, United States

THIS PROPERTY ONLY RENTS ON A FRIDAY TO FRIDAY SCHEDULE - 7 NIGHT MINIMUM REQUIREDbrbrROOM LAYOUT br1st Floor- Kitchen with Dining Area (the table has a leaf to expand and accommodate seating 6 comfortably), Living Room, Bedroom with Queen bed and 1 Twin bed with en suite tub-shower bathroom, Shared Laundrybr2nd Floor- 2 Bedrooms each with a Queen bed and en suite tub-shower bathroombrbrDOGS PERMITTED Sorry, Dogs are NOT permitted at this property.brbrWaterside Retreat boasts comfortable furnishings and is perfect for couples wanting their own bed & breakfast feel in a private property with Rockland Harbor views. The unit is shared property with a long term tenant on the otherside of the house. brbrJust a few hundred feet from the Rockland Public Landing, this property is perfect for those coming to experience the North Atlantic Blues Festival or the Lobster Festival held in July and August. Restaurants, art galleries, and shops are also just steps away.brbrA sandy beach on Rockland Harbor is located 300 yards from the property.brbr2023 Rockland City Permit: STR26-29

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Bath

Sleeps

$200.1

/ Nightly

Apartment

New England Farmhouse Loft

Rockland, Maine, United States

Classic White New England Farmhouse. Enjoy the newly built loft above the barn. A separate entrance leads you upstairs to your tranquil getaway. Cream colors and natural woods relax your mind. Large windows look out to treetops with the option to close with remote control blackout blinds. Loft has clean, well-equipped kitchen. As well as beautifully tiled shower/bath combo. White leather sectional is a cozy welcome for morning coffee or a fun evening of cocktails. Friendly, safe neighborhood close to town and walking trails.

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Bath

Sleeps

$581.59

/ Nightly

Condo

Oceanfront Condo overlooking Rockland Harbor and pier. Permit#STR22-30

Rockland, Maine, United States

Newly renovated waterfront condo/townhouse with incredible views of Rockland Harbor and the Jameson Point pier. Contemporary vibe with white-washed floors, sleek gas fireplace, stainless appliances and vaulted ceiling. Floor plan is perfect for a single person, couple or small family. All spaces are well proportioned and efficient.brbr1 bedroom and full bath on 1st floor and 2 bedrooms and full bath (en suite) on second floor. Lovely deck overlooking harbor and ocean. 2 car detached garage. Washer and dryer. Pleasant neighborhood with great streets for walking and Rockland Breakwater is literally just a minute away by foot! Samoset Hotel and restaurants just a short stroll away too.brbrThis is a very attractive and comfortable home convenient to Rockland, Camden and Pen Bay Hospital. Short and long term lease available. Fully furnished.brShort Term Rental Permit # STR19-71

Bed

Bath

Sleeps

$132.74

/ Nightly

Private Vacation Home

Charming In-Town Rockland Home

Rockland, Maine, United States

Located in the heart of Midcoast Maine, this charming home has it all! Spacious first floor, well-stocked kitchen, two-second floor bedrooms and bathroom, first floor room with additional futon. Gardens and a generous deck offer a peaceful retreat in which to enjoy a morning coffee, an afternoon BBQ, or a marshmallow roast around the firepit. In-season vegetables are free for the picking.brbrCentrally located, this home is only minutes away from Rockland Harbor, ferry rides to Vinalhaven, North Haven, Isleboro, and Monhegan Islands, a movie or concert at The Strand, one of the many spectacular museums in town, local wineries and breweries, restaurants galore, lighthouses, the beach or a local swimming hole. brbrHike to the top of Mount Battie or Beech Hill Preserve. Better yet, take in the 180-degree view of Penobscot Bay while attending a concert at the top of Beech Hill. Time your stay to experience Rockport's Donut Festival, Belfast's Art in the Park, the North Atlantic Blues Festival, Rockland's Lobster Festival, the Union Fair, Belfast's Ice Carving Championships, or Camden's U.S. Toboggan Championships.brbrAll this and more from your home away from home. Come, relax, and enjoy!! 30-night minimum required.

2

Bed

1

Bath

4

Sleeps

$739.11

/ Nightly

Cabin

Comfortable home near the beach - dog-friendly - full kitchen & washer/dryer

Rockland, Maine, United States

Montgomery Cottage is conveniently located in the historic and artful city of Rockland. A short walk away in this quiet neighborhood is the harbor, a park, the Coastal Children's Museum, and the Sail Power and Steam Museum. It is six blocks to the galleries, shops, and restaurants on Main Street. Montgomery is a cozy and completely renovated Cape with a fully modern kitchen and baths. The house has comfortable furnishings, plus a laundry room in the basement. There is a picnic shelter in the backyard for outdoor dining.brbrThings to KnowbrThis vacation home includes air-conditioning units in the bedrooms.brbrRockland STR Permit #STR26-20

3

Bed

2

Bath

6

Sleeps

$280.6

/ Nightly

Cottage

Lighthouse Lookout – Waterfront Cottage for Two with Harbor & Lighthouse Views

Rockland, Maine, United States

brOverviewbrLighthouse Lookout is a waterfront cottage designed for two, offering sweeping views of Rockland Harbor and the iconic Breakwater Lighthouse. From the private deck, watch lobster boats, ferries, and sailboats pass by throughout the day, then settle in for sunset over the water. Inside, oversized windows and a bright, open living space keep the harbor front and center, creating a relaxing coastal retreat in every season.brbrThe SpacebrThis thoughtfully designed one-bedroom cottage is ideal for couples seeking a quiet, scenic getaway. The open living area is oriented toward the water, with large windows that bring in natural light and uninterrupted harbor views. The bedroom offers a comfortable, restful space, while the layout provides everything needed for a simple and enjoyable stay. For those who like to cook, the cottage includes a fully stocked kitchen. brbrStep outside to the private deck, where you can enjoy morning coffee, evening meals, or time around the fire pit overlooking the water. The setting offers a unique combination of activity and calm, boats moving through the harbor by day, and peaceful coastal evenings at night.brLocationbrThe cottage is located about one mile from downtown Rockland, providing quick and easy access to restaurants, shops, galleries, and local attractions by car or bike. This location offers the best of both worlds, close to town, yet set apart enough to enjoy a quieter, more private waterfront experience.brbrAmenities & HighlightsbrDirect waterfront location with harbor and lighthouse viewsbrPrivate deck with outdoor seating and fire pitbrBright interior with large windows facing the waterbrOne-bedroom layout designed for two guestsbrFenced yard and dog-friendly accommodationsbrConvenient access to downtown Rockland (approximately one mile)brIdeal For Couples seeking a romantic coastal getawaybrGuests looking for a peaceful waterfront setting with scenic viewsbrTravelers who want proximity to town while enjoying a more private retreatbrDog owners looking for a welcoming, secure outdoor spacebrbrAdditional NotesbrThis property is best suited for two guestsbrA car is recommended for easy access to downtown and surrounding areasbrBetsy and Dwayne live next door in the main house with their friendly chocolate lab, Mabel. While Lighthouse lookout is listed as a new property on VRBO, we have been hosting this cottage for about four years through a previous rental site and have maintained an average 4.9-star rating across our reviews. We recently decided to take over the hosting ourselves so we can work more directly with our guests and ensure our cottage stays a special place to visit. We are nearby if anything is needed, but we always respect our guest’s privacy.

1

Bed

3

Sleeps

Exceptional(6)

$760.46

/ Nightly

Private Vacation Home

Harborside Cottage, walk to downtown

Rockland, Maine, United States

Rockland Permit# STR25-32brbrCoastal Charm Meets Convenience: Your Perfect Rockland Getaway!brbrEscape to the heart of Rockland, Maine, where the charm of the harbor meets the tranquility of coastal living. This beautifully furnished 3-bedroom home offers the ideal vacation experience, just a short walk from the vibrant harbor, bustling restaurants, museums, and downtown activities.brbrAbout the Home:brbrStep inside to find a bright, airy space featuring a coastal-inspired design with shiplap walls, wood floors, and nautical artwork that perfectly complements the stunning surroundings. The home boasts three comfortable queen bedrooms, each with its own serene atmosphere—ideal for relaxing after a day of exploring. You'll love the modern fixtures, stainless steel appliances, and subway tile showers—a stylish blend of form and function.brbrThe spacious deck is the ultimate spot to unwind, offering beautiful water views and a peaceful setting to enjoy morning coffee or evening sunsets. And when you're ready to venture out, you're just a stone's throw from everything Rockland has to offer.brbrWhy Rockland brbrRockland, Maine, is making waves and has recently been featured in Travel + Leisure and The New York Times as one of the top coastal towns to visit in 2025. Known for its rich maritime history, vibrant arts scene, and top-tier restaurants, Rockland is the perfect blend of small-town charm and cosmopolitan culture. Whether you're savoring fresh lobster at a local eatery, strolling through one of the many galleries, or simply watching the boats come and go at the harbor, you'll quickly fall in love with the area.brbrLocation, Location, Location:brbrShort walk to the harbor, downtown Rockland, and famous attractions like the Farnsworth Art Museum and The Maine Lighthouse Museum.brAccess to restaurants, galleries, and shops that have made Rockland one of Maine's hottest spots for art lovers and foodies alike.brJust minutes from Rockland Breakwater Lighthouse and some of the best coastal trails in Maine!brThis home is the perfect mix of peaceful retreat and exciting adventure. Whether you want to relax on the rooftop deck, walk to a local café, or explore the vibrant downtown, you're in the perfect spot to experience the best of both worlds.brbrBook Now and Start Making Memories in Rockland!brbrDon't miss out on your chance to stay in one of the most desirable vacation spots on the Maine coast. Whether you're here for a weekend getaway or a summer escape, this charming home offers everything you need for a memorable stay. Reserve your dates today and get ready to experience coastal bliss!

3

Bed

2

Bath

6

Sleeps

Vacation Rentals By Owner In Rockland, ME

$405.14

$336.08

$603.54

$359.62

$466.16

$255.06

$466.9

$386.8

$966.49

$484.25

$147.48

$95.92

$661.46

$463.81

$200.1

$581.59

$132.74

$739.11

$280.6

$760.46

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$581.59

$125.35

$132.74

$147.48

$163.50

$463.81

$200.10

$538.07

$466.16

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