
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

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.

RK North : All season Waterfront cottage with dock
Waterfront get away !You will love the cottage in any season - right on the pond! Enjoy a private dock, swimming and floating right at your door. Relax at the fireplace under twinkle lights , enjoy birdwatching, hiking and swimming during your stay. Lots of ATV and snowmobile trails near by. A close drive to Kennebunkport where your find beach’s , shops and restaurants galore. The cottage has 2 kayaks and a canoe for use during your stay. There are 2 Smart TVs for streaming. Shows and DVD

Plymouth's Historic Doll House; A tiny house
The Doll House has everything you’ll need at under 700 square feet. This fully-outfitted, historic, full-house rental has a complete kitchen, living room, two-bedrooms, bath, back sitting room, front farmer's porch and beautiful gardens and sitting areas. The Doll House is within easy walking distance to the Town Common, great restaurants and shopping, the Flying Monkey, and PSU. We are just a few minutes' drive to the Barn on the Pemi and Holderness School. NH Rooms Tax; License #059528.

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!

Unique Waterside Cottage - White Mountains, NH
Idyllic, serene waterside cottage. The private deck perched over the 32 acres of spring-fed, trout stocked-water is perfect for romantic sunsets. Enjoy the turtles as your feet dangle over the deck. The detailed cottage has wi-fi and comes with a well-equipped kitchen, and quality bedding, and is ideal for 2 people. Relax, read, fish, listen to the loons - a perfect get-away to completely unplug. Great hiking, kayaking, and biking in the area. Grill, hammock, and fire-ring by water's edge.

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!

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.
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

Wells Maine Home with a View

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

“Stay Awhile in the Lake's Region”

Jim's place

A: Cozy 2-BR Cottage Duplex - Unit A

A: Summer, Lake, Ski, Hike, Concerts

Cozy Maine Cottage by the Sea

Sunset Haven - Little Sebago Lake

Sawyer Lake Bear House

Cozy Cottage on Highland Lake
Private cottage rentals

The Lil'house - A Mountain Top Modern Cottage

King’s Cottage PERFECTLY LOCATED!

Sunrise at 15 Mills Road. Fully renovated Cottage.

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Peaceful Ossipee Lake Cottage Private Beach/Dock

5 Bedroom Cottage overlooking Ossipee Lake

Serene Lakefront Retreat in Southern Maine

Secluded Coastal Home & Cottage 3 Minutes to Beach
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 € 68 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 & child-friendly amenities

Wifi availability
10 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!
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- Rentals with a firepit Ossipee
- Rentals with lake access Ossipee
- Family-friendly rentals Ossipee
- House rentals Ossipee
- Rentals with a kayak Ossipee
- Pet-friendly rentals Ossipee
- Rentals with beach access Ossipee
- Cabin rentals Ossipee
- Waterfront rentals Ossipee
- Beachfront rentals Ossipee
- Rentals with outdoor seating Ossipee
- Rentals with a washing machine and dryer Ossipee
- Rentals with a patio 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
- Weirs Beach
- Pats Peak Ski Area
- Long Sands Beach
- Loon Mountain Resort
- Scarborough Beach
- York Harbor Beach
- Mount Washington Cog Railway
- Willard Beach
- East End Beach
- Short Sands Beach
- Tenney Mountain Resort
- King Pine Ski Area
- Cape Neddick Beach
- Gooch's Beach
- Cranmore Mountain Resort
- Franconia Notch State Park
- Gunstock Mountain Resort
- Omni Mount Washington Resort




