Waterfront vacation rentals in Ossipee

Find and book unique waterfront accommodations on Airbnb

Top-rated waterfront accommodations in Ossipee

Guests agree: these waterfront accommodations are highly rated for location, cleanliness, and more.

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Top guest favourite

Home in Wolfeboro

4.99 out of 5 average rating, 134 reviews

Tranquil Pondside Retreat

Welcome to this clean, bright, airy cabin with floor-to-ceiling windows and stunning views of Sargent's Pond in all seasons. At 62 acres and with just twelve homes, Sargent's Pond is the perfect place for simpler pursuits and peace and quiet. Enjoy two comfortable double bedrooms, a pull-out sofa in the living room, a bathroom with tub, washer, and dryer, a fully equipped kitchen with dishwasher, Wifi, bluetooth stereo system (bring your vinyl!), and Smart TV. Enjoy dining and relaxing on the spacious deck with commanding water views, and for the little ones, swinging and sliding on the swing set. Above the garage is a recreation room with a ping pong table as well as a smashing children's playroom filled with toys, board games, puzzles, and books. Enjoy the TV/ DVD player with a variety of favorite kids' flicks. Perfect for rainy days or down time, this extra living space is sure to please kids and adults alike! Please note that a pack-and-play, toddler mattress, and toddler high chair are available upon request.

Guest favourite

Home in Naples

4.99 out of 5 average rating, 149 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Top guest favourite

Cottage in Wakefield

4.99 out of 5 average rating, 100 reviews

Gorgeous Romantic Lakefront Getaway

Beautiful, 170 feet of waterfront Carriage House with a lovely sandy beach for a relaxing vacation in the Lakes Region of New Hampshire. Very close to the White Mountain National Forest, Kancamagus Highway, and several Ski Resorts. Within 45 minutes to the beaches of Maine and the Seacoast of New Hampshire. Our Carriage House is 1.5 hours from Boston and 2 hours from Worcester, MA. The Carriage House was built in 2021 with top-line finishes, fixtures, and furnishings for a romantic getaway.

Top guest favourite

Treehouse in Sanford

4.9 out of 5 average rating, 540 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Superhost

Cottage in Freedom

4.79 out of 5 average rating, 494 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Lakefront House, contemporary, amazing views, large deck, private lake beach & dock, steps from house (swimming). Very fast internet, multiple users. Private free parking. Fully equipped kitchen, AC, Smart TV & Modern shower room. Laundry Equipment, all Linen supplied. Sun trap West Facing Deck with loungers for relaxation. Canoe, life preservers & paddles included. 2 Fire pits & Grill. Boat put-in locally. Following cleaning codes: Airbnb & other authorities. Please ask any questions.

Top guest favourite

Home in Wakefield

4.98 out of 5 average rating, 178 reviews

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Book now and get 10% OFF for weekly or longer stays!

Guest favourite

Home in Bridgton

4.98 out of 5 average rating, 133 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

Guest favourite

Cottage in Middleton

4.96 out of 5 average rating, 198 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting!

Guest favourite

Cottage in Conway

4.95 out of 5 average rating, 371 reviews

20ft from the Water with Mountain View!

This cozy cottage sits 20 ft from Pequawket Pond. We are the only cottage in this association that has 2 floors and directly on the pond. It has a spiral staircase that leads downstairs to the bedroom downstairs with walk out access. We are located within minutes to the Mount Washington Valley and all the amenities the valley has to offer. Ski resorts galore! We also have a kayak and 2 paddle boards available for our guests to use!

Superhost

Home in Freedom

4.86 out of 5 average rating, 110 reviews

Cozy camp for swimming, water sports and more!

Our lake house is nestled into the woods with direct access to Ossipee lake. “The Pancake House” combines the best of a campy camp with modern amenities. The mountain view from the lake is stunning! Our game room, lakefront recreation options and two additional living rooms will keep everyone relaxed and entertained with plenty of space to relax and unwind. We are centrally located to many outdoor activities.

Guest favourite

Cabin in Parsonsfield

4.96 out of 5 average rating, 239 reviews

Riverfront cabin between Portland & White Mtns.

Look out onto the always-changing Ossipee River from this cute little log cabin. Use our tandem kayak, or fish and swim from our dock. In the winter months, ride your snowmobile right from the driveway, take a brewery tour in Portland, head to the White Mountains, or just watch the river go by. Cornish, Maine is just 12 minutes away and has plenty of dining and shopping opportunities.

Top guest favourite

Cabin in Jackson

4.95 out of 5 average rating, 138 reviews

Jackson Winter Wonderland - Wildcat/Attitash

Nestled in the picturesque town of Jackson, this charming log cabin offers a one-of-a-kind getaway experience. Surrounded by the stunning White Mountains and situated alongside the Ellis River with a refreshing swimming hole, this property is the ultimate retreat for those seeking tranquility and natural beauty. Located between Wildcat + Attitash for the perfect ski vacation.