
House holiday rentals in Ossipee
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Top-rated house rentals in Ossipee
Guests agree: these houses are highly rated for location, cleanliness and more.

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.

Perfect Family Getaway On Lake Ossipee
Our 10 year old home has four bedrooms three baths, theater room, gas fireplace, bar outdoor fire pit, open concept kitchen, nestled in a mountain landscape. Beautiful private beach with a playground, picnic area and boat launch only a short walk away. Tennis courts and a basketball court centrally located within the community. Boat rentals available on the lake. Multiple ski areas close by. Easy access to local and state snowmobile trails and the lake for ice fishing right out of the driveway.

Perfect NH Getaway Retreat in the White Mountains
Perfect getaway for any season! Ideal location in the heart of NH White Mountains & Lakes Region. The beauty of this NH getaway is that while you’re only a few miles from numerous winter and summer recreational activities, restaurants and shopping; our home and neighborhood are a quiet retreat from the hustle and bustle. Meticulously cared for and decorated with country charm, our home has a modern kitchen, large master bedroom, and best of all, your own re-created English pub for entertaining.

The ZEN welcomes you, your home away from home.
The goal is for you to relax, recharge, enjoy & breathe. We offer a private 3 person HOT TUB , seasonal outdoor warm shower& chiminea firepit , infrared SAUNA, 72" freestanding bathtub for the ULTIMATE spa experience. King bed with an adjustable & vibrating bed base. The cozy 600 sqf home is equipped with everything your heart could desire. Artistic Design around every corner. BOHO swings on the private porch. We abutt a 13 ac conservatory land with walking & hiking trails off the backyard.

Pet-friendly cabin with hot tub and beach access!
Feel right at home in our open-concept year-round vacation gem within the Chocorua Ski and Beach community half a mile from the Moore’s pond. The cabin is nestled in the woods providing privacy. It boosts a double-sided fire-place and hot tub perfect for the cooler nights, a wraparound deck, as well as an enclosed porch. On the basement level, there is a pull-out couch, bedroom, TV, and full bathroom allowing for extra hang out and sleeping space. Follow us on insta: #sandypinestamworthnh

Tranquility, Relaxation, Family, Romance
Bring your family or have a romantic getaway in this beautiful 2 bedroom, 2 private baths located in this quiet country setting. Pet friendly. Big fenced in wooded back yard for your pets to roam. Big back yard deck w/ seating, grill. Minutes away to boat launching area to rent party boats, kayaks, paddle boats, Swimming, winter sports on Milton 3 ponds. Seasonal blueberry, peach, apple picking in town. Park your boat or snowmobile trailors. Skydive New England right in town. Fall leaves.

Otter Ski/Walk to Village/Cozy 2 Bed/Hot Tub
Best location, directly in the village! Formerly the Otter Ski Club, restored with cozy, bedding & linens. Step to restaurants, North Conway CC, the Village green, scenic train station, coffee shops, shops, skating, & nightlife. I do prefer to book the entire house and only use the 2 bedroom lockoff to fill openings. Kayak the Saco, adventure parks, skiing, story land, hiking, etc. READ ABOUT THE SPACE- there could be other guests on the other side of the home. PETS NEED PRIOR APPROVAL

Cozy Guest Suite in White Mountain National Forest
Guest Suite, mother-in-law apartment with private entrance. One bedroom with living room, dining area, kitchen, stove, full refrigerator. WiFi and a futon couch that turns into a bed in the living room. The converted basement apartment is a comfortable, and cozy place to stay while visiting the Mount Washington Valley. Perfect for adventuring, climbers, hikers, bikers and skier/snowboarders. Have a hot pot of organic local coffee and get outside in the beautiful Mount Washington Valley!

Fall/Ski Fun: Spacious Home near downtown Meredith
My place is close to Mills Falls in Meredith, close to skiing, casual and fine dining, art shops, wineries, art and antique shops, just minutes to 2 - 4 hour hikes with great views of White Mountains and Lake Winnepesaukee, a beautiful Association Beach, and family-friendly activities. You’ll love my place because of the comfy bed, the kitchen, the high ceilings, its cleanliness, and coziness. My place is good for couples, solo adventurers, business travelers, and families (with kids).

Cozy Retreat-NEW Coffee Bar
Welcome to Buttercup Inn Tucked away in the peaceful lakes region, less than 2 miles from downtown Wakefield, this tastefully upgraded home may just surprise you. Every detail has been designed to make you feel right at home, from cozy furnishings to the brand new coffee bar- your go-to spot for a perfect brew. Whether you're unwinding or exploring the area, this charming retreat's proof that sometimes the best places are the ones you least expect. Message for further info.

Our Mountain Retreat – Lake Ossipee Access
Spacious 5 bedroom home with convenient lake access, just a short walk or 5-minute drive to beautiful Lake Ossipee. Enjoy easy proximity to King Pine Ski Area and a quick 25-minute drive to Conway, where you'll find outlet shopping, scenic hiking trails, and a variety of restaurants. This property features a large yard with a fire pit, and a hot tub for ultimate relaxation. The master bedroom includes a private deck—perfect for morning coffee or stargazing at night.

White Mt Retreat: New Kitchen, W/D
Get away from it all in our lovely, spacious home with its new kitchen, in Eaton, only 15 min to the shops and restaurants in North Conway and five minutes to King Pine Ski Area. Our place is ideal for outdoor enthusiasts, couples, chefs, and families. Our two floor home with two living areas is great for privacy and working remotely. Enjoy skiing at local peaks, hiking beautiful trails, warming in front of our fireplace or shopping in town. We are owner-operated
Popular amenities for house rentals in Ossipee
House rentals with a pool

Cozy & updated Loon MTN condo

Deer Park-Shuttle-Amenities- Fireplace

Walkable Downtown North Conway w private hot tub!

Spectacular log home with private pool and hot tub

Privacy, River, Pond, A frame Hot Tub EPIC Views,

Bear Brook House

Stylish Mtn Home-Ski/ Pools/ Hot Tubs & Fire Pit

Lovely 2 Bedroom Loft at Loon Mountain! Lincoln NH
Weekly house rentals

Camp Looney: Lake Access & Pet Friendly

4-Season Escape w/ Woodstove, Firepit & Mtn Views

Hot Tub•Yard•King Bed•15mins to North Conway

Renovated Luxury Lakefront w/ Beach/Dock/firepit

HTub | Rec Rm | Zen Deck | Tech Beds | Lake < 1mi

Spacious, renovated 2-bedroom home on golf course!

Log Cabin on the River w/ Private Hot Tub

Quaint Ossipee Home
Private house rentals

Cozy Cabin near Tuftonboro & Lake Winnipesaukee

Boutique Lakefront Cabin/ King Beds/ Pet Friendly

Cheerful 2 bedroom hilltop guest cottage with view

Peaceful Lakefront Retreat

Lake Winni home w/ hot tub & short walk to beach

Ski • Pets • Private Hot Tub • Ice Castles 25 mins

Downtown! Entire home w/ Tiki Bar & Grill!

The Retreat by White Lake
When is the best time to visit Ossipee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $306 SGD | $318 SGD | $305 SGD | $294 SGD | $308 SGD | $336 SGD | $360 SGD | $392 SGD | $340 SGD | $343 SGD | $312 SGD | $327 SGD |
| Avg. temp | -5°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 20°C | 16°C | 10°C | 4°C | -1°C |
Quick stats about house rentals in Ossipee

Total holiday rentals
Explore 80 holiday rentals in Ossipee

Nightly prices starting at
Ossipee holiday rentals start at $76 SGD per night before taxes and fees

Verified guest reviews
Over 2,510 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
80 of Ossipee holiday rentals include wifi access

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

4.9 Average rating
Ossipee stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with beach access Ossipee
- Cabin rentals Ossipee
- Rentals with a firepit Ossipee
- Family-friendly rentals Ossipee
- Rentals with lake access Ossipee
- Rentals with a washing machine and dryer Ossipee
- Waterfront rentals Ossipee
- Rentals with a fireplace Ossipee
- Pet-friendly rentals Ossipee
- Beachfront rentals Ossipee
- Rentals with outdoor seating Ossipee
- Rentals with a kayak Ossipee
- Cottage rentals Ossipee
- Rentals with a patio Ossipee
- House rentals Carroll County
- House rentals New Hampshire
- House rentals United States
- White Mountain National Forest
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Scarborough Beach
- Pats Peak Ski Area
- Long Sands Beach
- Loon Mountain Resort
- York Harbor Beach
- Weirs Beach
- Mount Washington Cog Railway
- King Pine Ski Area
- Cranmore Mountain Resort
- Tenney Mountain Resort
- Franconia Notch State Park
- East End Beach
- Omni Mount Washington Resort
- Willard Beach
- Short Sands Beach
- Diana's Baths
- Gooch's Beach
- Cannon Mountain Ski Resort




