
Cottage holiday rentals in Ossipee
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Top-rated cottage rentals in Ossipee
Guests agree: These cottages are highly rated for location, cleanliness and more.

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.

*5-Star CLEAN *Outdoor Shower *Private Yard & FUN!
This guesthouse is located in the beautiful and historic areas of Tamworth & Chocorua, NH. It features many inviting spaces where you can relax and enjoy the natural beauty & peaceful surroundings. The decor is travel-inspired and vibrant, creating a warm & fun atmosphere. You will love the two patios: one includes a grill and gazebo for outdoor dining, comfortably lit for evening use, while the other boasts a lovely porch and a fire pit area. The outdoor shower off the porch is truly amazing!

Cottage on the lake! Includes kayaks & rowboat!
Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, fenced in yard. Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided

Log Home Meredith NH Pet Friendly Custom Fire-Pit
Log home getaway in Meredith NH, near Lake Winnipesaukee! 4-night minimum in July & August 3-night minimum on holiday weekends 2-night minimum in the off-season Enjoy a peaceful stay in our cozy custom log home —just down the road from Lake Winnipesaukee! Our home offers a wraparound deck, outdoor fire pit, and is pet-friendly for up to two dogs. Only 3 miles to downtown Meredith, close to beaches, hiking, restaurants, spas, and breweries. Perfect for a relaxing escape with family and friends.

Eclectic Lakefront Cottage on Great East Lake
Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

Lake Winnie Cozy Cottage Getaway
Welcome to Lake a Dream… your spot for a fun filled family vaca on Lake Winnie in the summer or a cozy couples getaway in the winter! With just a quick 3 minute walk from the property you can enjoy some sunshine & sand on the beach! Or a 5 minute drive into downtown Wolfeboro to experience it’s charm; waterfront dining, ice cream, shops, cafés & more! For winter stays, cozy up by the fireplace with a cup of hot cocoa & some fun family games! The cottage is not far from Gunstock & Kingpine!

Beautiful Lakeside Cottage
Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

RiverPine Retreat - Clean & Bright Waterfront Home
Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

☀ 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. The sunsets can be unbelievable!

Private Beach, Lake Front, Family Friendly Cottage
Our clean private sandy beach, with a gentle slope is perfect for all swimmers. Sawyer Lake is a fun community. Enjoy our fun lakefront cottage with the perfect layout. 15 min. to Gunstock, Weirs Beach & Tilton Outlets • Kids will want to stay downstairs with a walkout, Foosball table, board games, TV, and 2 gaming systems [XBox 360° & Wii] with games. • Adults relax in peace upstairs with 2 private bedrooms, living area, & wood burning fireplace. Ask about weekends.

Taproot Cottage at Stone Mountain
Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

Lovely cottage on Sunrise Lake, Middleton, NH.
A lovely lake-front cottage with a private beach on quaint Sunrise Lake! The house has a great view overlooking the water. Enjoy a beautiful morning view of the sun rising onto the lake with a cup of coffee or tea, grilling a tasty dinner on the deck, and toasting marshmallows in the fire pit for dessert. We also provide a double kayak so you can explore the mile-long lake from the easy launch point in front of the house.
Popular amenities for Ossipee cottage rentals
Cottage rentals with a hot tub

Charming Cottage so close to JXN Falls & hiking!

Freshly Renovated, Family-Friendly Coastal Cottage

Cozy Cottage on a Lake, near Gunstock Mountain

Cozy cottage near Gilford, lake access & hot tub!

Fully Renovated/4min to K-port/HotTub/Game Room

Wells Maine Home with a View

The Loon Nest, Waterfront Lake House, Wood Hot Tub

Contemporary Cottage With Ocean View 13
Pet-friendly cottage rentals

Bright, clean, private cottage near Higgins Beach!

Cozy Cottage w/ Lil' Pond, Fenced Yard & Firepit

Deja Blue~Guesthouse-Maine’s Best Oceanfront view!

A: Summer, Lake, Ski, Hike, Concerts

Sawyer Lake Bear House

True Maine Artist Cottage with Outdoor Shower

Sweet cottage in quiet convenient coastal setting.

Rustic Pebble Cottage in beautiful Bridgton, Maine
Private cottage rentals

Rustic Cabin w/ SUP boards, Kayaks, Canoe, Firepit

The Lil'house - A Mountain Top Modern Cottage

Cottage at Footbridge Beach Ogunquit

Charming 3 bedroom cottage on Notched Pond

Completely updated detached cottage/Paugus Bay!

Peaceful Ossipee Lake Cottage Private Beach/Dock

5 Bedroom Cottage overlooking Ossipee Lake

Peaceful Lakeside Maine Retreat
Quick stats about cottage rentals in Ossipee

Total holiday rentals
Explore 10 holiday rentals in Ossipee

Nightly prices starting at
Ossipee holiday rentals start at $111 AUD per night before taxes and fees

Verified guest reviews
Over 1,100 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Wi-Fi availability
10 of Ossipee holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Ossipee rentals

4.8 Average rating
Ossipee stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with a fire pit Ossipee
- Waterfront rentals Ossipee
- Rentals with a fireplace Ossipee
- Beachfront rentals Ossipee
- Rentals with outdoor seating Ossipee
- Rentals with beach access Ossipee
- Cabin rentals Ossipee
- Rentals with a patio Ossipee
- Family-friendly rentals Ossipee
- House rentals Ossipee
- Rentals with a kayak Ossipee
- Pet-friendly rentals Ossipee
- Rentals with a washing machine and dryer Ossipee
- Rentals with lake access Ossipee
- Cottage rentals Carroll County
- Cottage rentals New Hampshire
- Cottage rentals United States
- White Mountain National Forest
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Long Sands Beach
- Pats Peak Ski Area
- Loon Mountain Resort
- Scarborough Beach
- York Harbor Beach
- Mount Washington Cog Railway
- Willard Beach
- Short Sands Beach
- East End Beach
- Cape Neddick Beach
- Tenney Mountain Resort
- Franconia Notch State Park
- King Pine Ski Area
- Gooch's Beach
- Omni Mount Washington Resort
- Gunstock Mountain Resort
- Cranmore Mountain Resort





