
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.

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

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.

The Lake house
Enjoy the southern exposure, a sugar sand walkout beach, an L-shaped dock, and classic Lake Winnipesaukee construction. The open concept includes a full kitchen and a living room. The spacious bathroom also includes a washer and dryer. It has one private bedroom, and a ships ladder guides you to a loft containing additional sleeping space, with a catwalk to a private balcony overlooking the lake. This property has a detached bunkhouse with two full-sized beds and a ¾ bath.

☀ 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!

Cozy, Pet-Friendly Escape Near Lake & Mountains
Nestled between Gunstock Mountain and Lake Winnipesaukee, Hidden Creek Cottage is your perfect year-round getaway. This airy, sun-filled home features high ceilings, a newly updated kitchen, gas fireplace, central air, king size bed, and laundry. Step outside onto a brand new expansive deck built for outdoor dining and entertainment, make your way down to the fire pit for stories and s'mores and enjoy the sunset while listening to the tranquil sounds of our hidden creek.

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.

Tiny Lakefront Cottage
Escape to our beautifully redesigned cottage on serene Pequawket Pond, nestled in the heart of New Hampshire's White Mountains. This studio, one of just seven in a private association, offers maximized comfort and space just steps from the water. Enjoy complimentary use of our kayak and two paddleboards, or simply unwind on the patio with grill, soaking in the breathtaking pond views. Your perfect lakeside retreat awaits!.
Popular amenities for cottage rentals in Ossipee
Cottage rentals with a hot tub

Charming Cottage so close to JXN skiing & hiking!

Freshly Renovated, Family-Friendly Coastal Cottage

Cozy Cottage on a Lake, near Gunstock Mountain

Cottage in the Pines | Lakeside + Sauna + Hot Tub

Gunstock, skiing, hot tub, lake access & fire pit

Paradise Found Minutes from Ogunquit | Heated Pool

Waterfront Getaway w/ Private Beach (HOT TUB)

The Loon Nest, Waterfront Lake House, Wood Hot Tub
Pet-friendly cottage rentals

“Stay Awhile in the Lake's Region”

Welcome to Lakota! A Cozy 2 BR Cottage.

Family & Pet Friendly, Lakefront Home

A: Cozy 2-BR Cottage Duplex - Unit A

A: Summer, Lake, Ski, Hike, Concerts

RK North : All season Waterfront cottage with dock

True Maine Artist Cottage with Outdoor Shower

The red house
Private cottage rentals

The Lil'house - A Mountain Top Modern Cottage

Cozy Cottage on Paugus Bay

Lakehurst Lakefront Cottages #5

King’s Cottage PERFECTLY LOCATED!

The Cozy Cottage at Loon Pond, Netflix

Big Pine Cottage Lakefront Dock Kayaks & Firepit

Serene Lakefront Retreat in Southern Maine

Cozy Lake Access Cottage With Deck.
Quick stats about cottage rentals in Ossipee

Total holiday rentals
Explore 20 holiday rentals in Ossipee

Nightly prices starting at
Ossipee holiday rentals start at $103 SGD per night before taxes and fees

Verified guest reviews
Over 1,150 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
20 of Ossipee holiday rentals include wifi 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!
Destinations to explore
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- Beachfront rentals Ossipee
- Rentals with outdoor seating Ossipee
- Rentals with lake access Ossipee
- Rentals with a firepit Ossipee
- Rentals with a kayak Ossipee
- Rentals with a patio Ossipee
- Family-friendly rentals Ossipee
- House rentals Ossipee
- Waterfront rentals Ossipee
- Pet-friendly rentals Ossipee
- Rentals with beach access Ossipee
- Cabin rentals Ossipee
- Rentals with a washing machine and dryer Ossipee
- Rentals with a fireplace 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
- Pats Peak Ski Area
- Weirs Beach
- Loon Mountain Resort
- Long Sands Beach
- Scarborough Beach
- York Harbor Beach
- Mount Washington Cog Railway
- Cranmore Mountain Resort
- Tenney Mountain Resort
- Willard Beach
- King Pine Ski Area
- Short Sands Beach
- Franconia Notch State Park
- Cape Neddick Beach
- Gunstock Mountain Resort
- Omni Mount Washington Resort
- Gooch's Beach
- East End Beach




