Home Vacation Home Rentals By Owner In Wolfeboro, NH

Showing 40 Of 50 Vacation Rentals
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$1402.46

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Private Vacation Home

Classic Lake House with Guest Cottage on Wolfeboro's Premier Springfield Point

Wolfeboro, New Hampshire, United States

Charming Lakefront Family Compound on Delings CovebrDiscover the perfect family getaway at this delightful lakefront compound on Lake Winnipesaukee, offering a spacious main house, a cozy guest house, and all the amenities you need for a relaxing vacation. With a large lawn, sandy beach, and excellent docking, this property is ideal for making lasting memories on the water.brMain Housebr3 Bedrooms, 2 Baths: Two bedrooms feature air conditioning for added comfort.brCozy Living Room: Relax by the fireplace after a day on the lake.brScreened Porch & Large Deck: Perfect for outdoor dining or simply enjoying the peaceful surroundings.brRustic Charm: Knotty pine interiors add warmth and character to the space.brGuest Housebr2 Bedrooms, 1 Bath: Comfortable accommodations for additional family members or friends.brFull Kitchen: Fully equipped for convenience during your stay.brSteps Away: Located just a short walk from the main house for easy access while maintaining privacy.brOutdoor FeaturesbrSandy Beach & Large Lawn: Ideal for swimming, sunbathing, and outdoor games.brGood Docking: Secure space for your boat and easy lake access.brSerene Setting: Enjoy laid-back comfort with stunning views of Delings Cove.brConvenient LocationbrA short boat or car ride takes you to downtown Wolfeboro, where you can explore shops, dine at local restaurants, attend concerts, or stroll through the historic village.brThis property combines rustic charm with modern conveniences, making it the perfect destination for a relaxing and fun-filled lakeside vacation. Reserve your stay today and start creating unforgettable memories!
Bed 5

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Bath 3

Bath

Sleep 13

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Exceptional(5)

$2694.41

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Private Vacation Home

Lake Winnipesaukee Waterfront Rental Wolfeboro NH Dock Sleeps 13

Wolfeboro, New Hampshire, United States

Property Owner has JUST made available the week of July 4th to July 11th!brbrLake Winnipesaukee waterfront cottage located in Wolfeboro, New Hampshire offering beautiful lake views, a large dock, private sandy beach, and timeless vintage lakehouse charm just one mile from downtown Wolfeboro. Known as “Windemere,” this historic waterfront home blends nostalgic character with modern comforts, creating a setting designed for relaxing and making lasting memories in the Lakes Region.brbrOriginally built in 1919, the home features classic architectural details including wainscoted walls, a beautiful stone fireplace, large bedrooms, and multiple porches that invite you to slow down and enjoy lakeside living. Gather around the large dining room table, reconnect on the three-season porch, or enjoy quiet mornings with coffee by the water as loons call across the lake.brbrThe waterfront setting includes a level front yard ideal for outdoor recreation, a private sandy beach, and a large dock partially covered with an awning that provides both sun and shade seating. The dock accommodates two boats up to 24 feet in length each, making boating and swimming easy and convenient.brbrWhile maintaining its vintage character, the home includes modern conveniences such as a well-equipped kitchen, newly renovated bathrooms, cable TV, Wi-Fi, and a washer and dryer to ensure a comfortable stay. A lakeside hammock offers the perfect place to relax with a book and take in the peaceful surroundings.brbrLocated just one mile from downtown Wolfeboro, affectionately known as “The Oldest Summer Resort in America,” guests enjoy easy access to shops, restaurants, bakeries, ice cream, and year-round Lakes Region activities by car, boat, or even on foot.brbrPlease note: The kayaks pictured in the listing photos are not included with the rental and are not available for guest use.brbrLinens: Sheets, bath towel sets and arrival bedmaking service are all included with this rental. This DOES NOT include beach towels.brbrPlease note: Amenities and furnishings can change at any time without notice. At Owner discretion, exterior cameras may be in place now or in the future.brbrThis property is managed by At The Lake Vacation Rentals, LLC. State of New Hampshire Meals and Rentals Tax Operator's License #058822.
Bed 6

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Bath 4

Bath

Sleep 13

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$2096.23

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Private Vacation Home

Exceptional Lakefront Home on Springfield Point – Lake Winnipesaukee

Wolfeboro, New Hampshire, United States

Exceptional Lakefront Home on Springfield Point – Lake WinnipesaukeebrNestled at the tip of Springfield Point, this stunning lake house offers some of the best views of Lake Winnipesaukee and the surrounding mountains, with breathtaking sunsets every night of the year. With 185 feet of private waterfront, you’ll enjoy your own slice of paradise, featuring a true sandy beach, a lush lakeside lawn, and a dock where you can relax all day in full sun.brThe property is equipped with a boathouse, dock, and breakwater, providing protected docking for up to three boats—perfect for water enthusiasts. Whether you're swimming, boating, or simply lounging by the water, this location offers everything you need to enjoy the ultimate lakeside lifestyle.brInside, the home is thoughtfully designed for comfort and relaxation. The first-floor master bedroom features a king-sized bed and a newly renovated, luxurious bathroom. Two additional bedrooms are located on the main level—one with a queen-sized bed and the other with a king —ensuring ample space for guests.brIn the walkout lower level, you'll find a spacious bedroom with a queen, a full, and one twin, as well as a laundry area and a cozy den for additional relaxation.brThis exceptional lakefront home is the perfect setting for creating lifelong memories. Whether you're enjoying the sunsets from the deck, playing by the beach, or simply unwinding in comfort, this is the ultimate lakeside retreat.brbrWater trampolines are not allowed at this property.
Bed 4

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Bath 3

Bath

Sleep 10

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Exceptional(28)

$708.72

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Private Vacation Home

Luxurious Lakehouse - Firepit with beautiful sunsets+ Central Air + Private Dock

Wolfeboro, New Hampshire, United States

Crystal clear Rust Pond contemporary waterfront home with picturesque lake views from every angle and multiple decks. Your vacation home has central AC for hot days and a cozy gas stove and central heat for chilly nights. There is also a patio area to hang out and play corn hole and enjoy the views of the lake. The firepit is perfect for smores during those cool nights. Rust Pond is an oligotrophic lake with excellent swimming, SUP boarding, kayaking, fishing, etc. The home offers privacy in a peaceful lakeside setting, yet is just 10 mins from Wolfeboro downtown restaurants, farm to table fare, art galleries and boutique shopping.brbrIn the fall, the beautiful foliage is all around you and you can still get out onto the water to experience fall on the lake. The crisp weather is also perfect for local hikes and enjoying the firepit area.brbrIn winter the lake freezes over, providing opportunities to explore the lake like never before - ice fishing, walking, snowshoeing, skating, or cross country skiing. brbrSewall woods (5mi) provide miles of groomed cross country skiing trails and snowshoeing paths. Nordic Skier Sports (4mi) provides the rentals and trail pass you need to enjoy a day out snowshoeing or cross country skiing. brbrWe are also (6mi) from Abenaki, (20mi) from Gunstock & (29mi) from King Pine for skiing, snowboarding and snowtubing fun! Once back home snuggle up with a hot chocolate next to the gas stove and admire the views. brbrSUMMER ACTIVITIES:brbrGOLFING:brKingswood Golf Club (2 mi), Lake Winnipesaukee Gold Club (6 mi), Farmington Country Club (21 mi)brbrHIKING:brBrewster Heath Preserve Walking Trail (2 mi), Sewall Woods (5mi), Mt Major ( 14.5 mi), Plummer's Ridge Forest & Farm Hiking Trails (17 mi), Castle in the Clouds (20 mi)brbrWATER ACTIVITIES:brWake Winni (2 mi), US Postal Service Delivery Boat (2 mi), Mt Washington Boat Cruise (2 mi), Goodhue Boat Rental (5 mi)brbrbrWINTER ACTIVITIES:brbrSKI RESORTS:brWolfeboro Abenaki Ski Area(6 mi), Gunstock Mountain Resort(22 mi), Cranmore Ski Resort(45 mi), Attitash Resort(52 mi), Ragged Mountain Resort(55 mi)brbrCROSS COUNTRY SKIING/SNOWSHOEING:brSewall Woods (5mi)brNordic Skier Sports (for full ski and snow shoe rentals) (4mi)brbrATTRACTIONS:brSanta's Village in Jefferson, NH (92 mi)brJourney to the North Pole in Conway, NH (45 mi)brbrWolfeboro:brATTRACTIONS:brWright Museum of World War II (4 mi), Castle in the Clouds - Lucknow Mansion (20 mi), North Conway Shopping Outlets (50 mi), Storyland Childrens Amusement Park (50 mi), Santa's Village (92 mi)brbrRESTAURANTS - DOWNTOWN WOLFEBORObrMarker 21, El Centenario, Seven Suns Cafe, Garwoods, Nolans Brick Oven Pizzeria, Wolfeboro Dockside Grill and Dairy Bar, Bayside Grill and TavernbrbrBREWERIES AND WINERIESbrLone Wolfe Brewing Company (4 mi), Gilmanton Winery and Restaurant (26 mi)brbrbrThe Space:brbrThe house is freshly remodeled: light, airy, modern and beautiful with vaulted ceilings, large windows overlooking the lake from just about every room and streams of natural lighting. Your lakefront home away from home has been stylishly redesigned with high end furnishings and artistic touches for your iconic NH getaway.brbrWe have 4 decks, all with water views:br1st right off the kitchen with a dining table and chairsbr2nd right in front of the living room with 4 lounger chairsbr3rd right in front of the lower level br4th is a stand alone deck right over the stairs with a sectional seating arrangement and large umbrella for sunny daysbrbrEvery season on Rust pond has its own charm. In the summer your family can enjoy cooling off in the lake. Autumn brings a crispness to the air and beautiful views of the fall foliage. In winter the lake freezes over, providing opportunities to explore the lake like never before - walking, snowshoeing, skating, or cross country skiing. Once back home snuggle up with a hot chocolate next to the gas stove and admire the views.brbrWe provide outdoor toys for your enjoyment: 2 stand-up paddle boards, 1 kid kayak, 1 single adult kayak, 2 person inflatable kayak and a floating rubber dockie mat. Rust pond has some great fishing, which you can enjoy right from the dock. Plenty of life jackets available and recommended when using water toys.brbrThe living area features long, light filled windows overlooking the magnificent lake, plush leather sofa, and 2 comfy swivel egg chairs. There is a West Elm double chaise to relax, read and take in the view. Wifi available throughout the property including the decks. We also have central air and heat to keep you comfortable throughout the stay. The lake house has lots o’ board game and books for all ages.brbrThroughout the house we have Casper mattresses for the most comfortable sleep during your stay. On the main floor are 2 bedrooms and a full bath. The second floor is an open loft overlooking the lake with a master en suite. The walkout lower level has an office with a Joybird Eliot Sleeper Sectional that pulls out into a queen foam mattress bed and a private full bath. The house comfortably accommodates six (6) people. brbrWe have 2 Bedrooms, 1 loft, one lower level room that can serve as bedroom or office and 3 full bathrooms:br(1) Master bedroom with King-Sized Bed, full bathroom and majestic views of water from the Loftbr(2) A bedroom with 2 full size bedbr(3) A bedroom with bunk beds - full and twinbr(4) Lower level room with Joybird Eliot Sleeper Sectional that pulls our into a queen foam mattress bed and panoramic views of the lake and a private bathroombrPlease bring your toiletries & beach towels.brbrA Chefs Kitchen ~ fully equipped with custom cabinets, granite countertops stainless steel appliances including a gas range, microwave, fridge/freezer, dishwasher, coffee maker, toaster, blender, cookware, dish ware, and flatware. Tea, coffee, basic spices and condiments included ~ we hope you enjoy! brbrPlease Read:brDO NOT CONSIDER THIS SITE IF YOU ARE HOSTING A PARTY OR EVENT. GROUPS OF 10 OR MORE ARE NOT ALLOWED. DISRUPTIVE NOISE LEVELS/MUSIC AT ANY TIME OF THE DAY GRAVELY JEOPARDIZE OUR FRIENDLY NEIGHBORHOOD RELATIONSHIPS AND WILL NOT BE TOLERATED. LAW ENFORCEMENT WILL BE CALLED IN & A NEGATIVE REVIEW WILL FOLLOW. WE KINDLY APPRECIATE YOUR CONSIDERATION ~brbrGuest Access:brThe entire unit is yours during your stay. Prior to your arrival, you will receive a unique entry code for the unit front door so no need to worry about losing keys!brbrOther details:brTHERE ARE PARKING SPACES FOR 4 VEHICLES. THERE IS AN ADDITIONAL FEE FOR EACH ADDITIONAL GUEST BEYOND SIX.brbrThere are three security cameras on the property, one in the driveway above the garage, one under the deck facing the lake, and one at the front entrance to the house.brbrPLEASE include a few words about you and your guests ~ we love knowing a little about our visitors!brbrNo parties, no smoking and no animals. We cannot allow pets as our son is highly allergic to dander.brbrNeighborhood description:brbrThe beautiful town of Wolfeboro is 10 minutes away with all the Lake Winnipesaukee activities available there including: Mt. Washington boat cruises from the town docks throughout the day, water sports by Wake Winni, boat rentals at Goodhue Boat Company, concerts in Cate Park, Great Waters Musical Performance, Craft Fairs, and the famous Huggins Hospital Fair. In town you will also find “The Nick” recreation area and the Pop Whalen indoor ice rink. Our family has loved walking around downtown to enjoy the ice cream shops and the local bookstore.brbrThere are 3 golf courses within 10 miles, with the closest being the Lake Winnipesaukee Golf Club - only 5 minutes away. The Cotton Valley Trail and the Ellis R. Hatch Jr. Wildlife Area are less than 5 miles away. For a good day hike, Mount Major in Alton offers a great family hike with breathtaking views of Lake Winnipesaukee and the Presidential Range, and is only 20 minutes away. Castle in The Clouds is also a favorite, with guided hikes for all ages and tours of the famous Lucknow Mansion. The hiking covers over 1000 acres of protected land, and has great views of waterfalls, rivers, and the surrounding lakes.brbrIf you are heading north, within one hour you can reach the Kancamagus Highway and the White Mountains, Story Land kids amusement park, and the Conway outlets for some great shopping.br
Bed 4

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Bath 3

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Sleep 6

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$2449.15

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Private Vacation Home

Luxury Lake Winnipesaukee Estate | Private Acre+ Waterfront Retreat

Wolfeboro, New Hampshire, United States

Experience lakefront living at its finest at this exclusive South Wolfeboro Bay estate—complete with your very own private, gradual sandy beach. Set on over an acre of premier Lake Winnipesaukee waterfront, this extraordinary home offers rare privacy, high-end comfort, and effortless access to the lake’s most desirable waters. Perfect for multi-generation vacations, family gatherings, and unforgettable summer memories.brInside, guests will appreciate expansive living spaces, reclaimed barn wood floors, custom wrought-iron railings, and floor-to-ceiling windows that frame sweeping lake views. The gourmet kitchen features premium appliances, granite countertops, and a spacious eight-person island—ideal for cooking, entertaining, and gathering with family and friends. Every level of the home is designed to welcome guests in style.brThe luxurious primary suite includes a private balcony overlooking the water—perfect for morning coffee or sunset unwinding. Additional well-appointed bedrooms and living areas ensure plenty of space for everyone to relax in comfort.brbr**no multi-week rentals allowed**brbrbrStep outside to enjoy spectacular outdoor living: a large lakeview deck, a screened porch, beautifully manicured grounds, and 155 feet of pristine waterfront with an exceptional walk-in sandy beach. Swim, paddleboard, boat, or simply unwind on the shoreline—this property is truly a lakeside playground. Ample parking and a bold stone wall add to the estate’s appeal and convenience.brLocated in the heart of Wolfeboro—America’s Oldest Summer Resort—this home offers easy access to dining, shopping, walking trails, golf, skiing, and year-round Lakes Region recreation. Just a quick boat ride or short drive to downtown Wolfeboro, it’s the perfect blend of seclusion and convenience.brA rare rental offering on Lake Winnipesaukee—ideal for guests seeking luxury, comfort, and a true waterfront experience. Let your lakeside vacation begin.
Bed 5

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Bath 5

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Sleep 14

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$1239.57

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Private Vacation Home

Escape from it all! Dock, beach & sunsets in south Wolfeboro #501

Wolfeboro, New Hampshire, United States

Spacious Lake Winnipesaukee Retreat with Stunning ViewsbrEscape to this private and spacious 4-bedroom, 3-bath lakefront home featuring all modern amenities, including central A/C, and located just two miles from the heart of Wolfeboro. Perfect for families or groups, this home offers an ideal combination of comfort, convenience, and breathtaking scenery.brProperty HighlightsbrOpen Floor Plan: Enjoy a bright, airy main living area with a seamless flow between the living room, dining area, and kitchen.brWraparound Deck: Take in spectacular lake and mountain views from the expansive deck, perfect for relaxing or entertaining.brSunny Southwest Exposure: Bask in all-day sunshine and end your day with stunning sunsets over Lake Winnipesaukee.brLandscaped Yard: Beautifully maintained with stone patios, a lush lawn, a small sandy beach, and a large U-shaped dock, ideal for boating or water activities.brAccommodationsbrMain Level: One bedroom with a queen bed and nearby full bath.brUpper Level: Private bedroom with a queen bed and en-suite bath.brLower Walkout Level: Two additional bedrooms – one with a queen bed and another bunkroom featuring a twin and bunk beds. The lower level also includes extra living space for games, lounging, or family time.brLocation & ActivitiesbrLocated just 2 miles from Wolfeboro center, with sidewalks the entire way for an easy walk or bike ride.brEnjoy prime waterskiing right off the dock or explore the surrounding area with a short drive to local shops, restaurants, and attractions.brThis lakefront retreat is the perfect place to create lasting memories, whether you're lounging by the water, enjoying outdoor activities, or exploring the charming town of Wolfeboro. Reserve your stay today!
Bed 4

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Bath 3

Bath

Sleep 10

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Exceptional(18)

$627.09

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Private Vacation Home

Lake Wentworth Estate: Unobstructed Sunset Views, Private Beach, Fire Pit, Lawn

Wolfeboro, New Hampshire, United States

This house is NOT listed on Craigslist. brbrExclusive - Sunset Point - Lake Wentworth home with generous dock and expansive lawn. Enjoy a quiet morning by the lake away from it all as you live just steps from the lake shore. Vivid unobstructed sunsets abound.brbrThis classic lake home faces west with stunning views of Lake Wentworth and the mountains beyond. The spectacular lakeside setting is the perfect place for swimming, canoeing, kayaking, fishing, and all sorts of water activities. Relax on the swim raft, or head out on your boat to enjoy the lake. Pontoon boat rentals from Melvin Village Marine - book early. Fishing on Wentworth is a favorite pastime and the lake is known for its Smallmouth Bass. Bring your boat and come right up to the generous dock. Included in the rental is use of the kayaks and there is a fishing boat and paddle board available for rent.brbrThe main home has three bedrooms and a loft. The master hosts a queen bed, with en suite master bath with a heated floor, while and the second large bedroom has a queen bed and a full bed. The third bedroom has two queen beds and a full bed in the loft which is great for kids. There are 6 separate beds in 3.5 sleeping areas and rentals are limited to 10 guests. brbrHoneymoon Hall: An additional bedroom with Ethan Allen queen bed and full bed with basic bathroom and shower allows for 2-4 extra guests for a maximum of 12 total. Private deck and beautiful french doors look out to the lawn and the lake beyond. A cute place to get away from the chaos of vacation.brbrFor larger groups - An additional 2 bedroom house for 6 people may be available and booked on VRBO as listing #3082890 or by contacting the owner with this listing. Maximum 18 guests. brbrThe kitchen is fully equipped with a stove, double oven, microwave, generously sized refrigerator, cookware, and utensils. There is also a gas grill on the porch. The oversized glass sliders and bay window provide wonderful views from the great room and the large enclosed porch connects you with the outdoors with added seating for big dinner gatherings. brbrA wood stove set in the fireplace helps set the mood for relaxation and country living on a cool night, but fast cable internet and WIFI are available for your evening enjoyment. A fire pit is available by the lake for you to sit in the evening and cook S'mores and if you happen to have a cloudy day, a 65 inch QLED TV is there for your enjoyment. brbrOptional: Paddle Boards, sunfish sailboat, fishing boat brbrThe lake itself is about five by three miles with many islands and a nature preserve, Stamp Act Island, in the middle. It is known for its tranquility and the superb water quality, perfect for a peaceful vacation. Just a few minutes from downtown Wolfeboro, the house is close to shopping, fine dining and casual restaurants, golf, walking/hiking trails, museums, and all the activities provided by Lake Winnipesauke and the Lakes Region, yet away from the noise and crowds of the bigger lake.brbrKeywords: Cottage, Lake Wentworth, Beach, Wentworth, privacy, family friendly, Lake Winnipesaukee Area, Wolfeboro, Best Lot on the Lake.
Bed 4

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Bath 3

Bath

Sleep 12

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Exceptional(35)

$540.69

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Private Vacation Home

Lakefront Family Retreat in Wolfeboro

Wolfeboro, New Hampshire, United States

Unwind and make lasting memories at this serene Crescent Lake escape, nestled on a sparkling, one-mile lake with kayak access to the stunning Lake Wentworth. This property offers something for everyone: float in the lake, lounge on the dock, or find your perfect spot in the sun or shade. A charming fishing jetty, a cozy hideaway hammock, and a grassy yard perfect for lawn games and BBQs add to the outdoor fun.brbrThe HomebrbrMaster Bedroom: Queen-sized bed with breathtaking lakefront views.brSecond Bedroom: Twin bunk beds for the kids or young at heart.brThird Bedroom: Two twin beds convertible to a king, also with serene lakefront views.brbrNewly added deck features panoramic lake views, inviting seating, and a dining table for eight—perfect for alfresco meals or evening cocktails. Plus, a covered patio beneath the deck lets you savor the fresh air and lake views, rain or shine.brbrThe main floor boasts an open-concept kitchen, dining, and living area, plus a tranquil sunroom. The lower level offers a family room, a convenient half-bath, and a full walkout slider to a patio leading to the lake—ideal as a private suite or extra living space.brbrExplore the AreabrTake a scenic 1.5-mile stroll along the Cotton Valley Rail Trail, which leads you directly to Wolfeboro’s town docks, shops, and restaurants on Lake Winnipesaukee. From waterfront dining to boutique shopping, there’s something for everyone.brbrAs day turns to night, enjoy stunning sunsets over the lake and gaze at star-filled skies—perfect for photographers and stargazers alike.brbrBook your Wolfeboro getaway and discover the perfect blend of relaxation and adventure at Crescent Lake!
Bed 3

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Bath 2

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Sleep 6

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