
Vacation rentals in Ossipee
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Top-rated vacation rentals in Ossipee
Guests agree: these stays are highly rated for location, cleanliness, and more.

Rustic Rose Cottage of Historic West Lebanon
Rustic guest suite on serene four acres. Abutting colonial cape style house and West Lebanon Historic District date back to early 18th Century. Private parking & entrance, queen memory foam mattress, steam sauna, kitchen and laundry supplies, and desk and high speed wifi for telework. Minutes from Skydive New England, Prospect Hill Winery or McDougal Orchard. 30min to Portsmouth NH, Maine beaches, and Lake Winnipesaukee. Just over an hour to the White Mountains, Portland ME or the Boston area.

Rustic Mountainside Chalet
Located on a wooded mountainside in the White Mountains & the Lakes Region of NH, close to hiking, 5 minutes to the rivers and 15 minutes to Lake Chocorua and Lake Ossipee for swimming/kayaking/tubing or just relax and enjoy the views of the mountains. Peaceful Chalet with one bedroom with one bunk bed unit with queen mattresses, and a large master bedroom loft with Cali King, kitchen, and 2 x bathrooms, a deep jetted tub. The basement is converted into an in-law’s suite where my parents live.

Luxurious Mountainside Cabin! Fantastic Views!
Cozy Cabin with Sweeping Mountain Views! A great escape with total privacy. Relax by the Fire Pit overlooking the Mountains! Head up to North Conway to the White Mountains or go South to the Lakes Region. Then escape the traffic and retreat to the quiet of your Mountainside Cabin. Wood Fired Sauna on the premises! We provide everything you will need for your stay, and I mean everything, just bring a sense of adventure! Pets Welcome! *Pet Fee Applies! *Additional Fee for Sauna

Clean, quaint studio apartment on small farm
Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

1BR cozy, luxurious getaway @ Krista's Guesthouse
Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Cluck's Cabin-Lakes/Mt Wash Valley
Adorable, obsessively clean, Cabin set in the Lakes Region and Mount Washington Valley. Set on almost 2 acres, you'll have a view of the mountains and wooded meadow that changes by the minute. Huge wrap around deck, firepit under the stars. Great Hospitality! Short stays available Thinking about two or more nights over Veteran's Day Weekend? Please inquire - discount available We offer early check in / late check out as often as possible. Let's discuss when you inquire.

Mountain Treehouse Guesthouse
Spacious second story post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

The Village House
Welcome to our recently renovated home , built in the late 1890's in the heart of beautiful Tamworth Village, right on quiet Main st. A quick 5 minute walk to "downtown", Remick Farm and museum, Barnstormers summer theatre and The Other Bakery. Tamworth is home to many local hiking trails from easy walks to over 4000 foot summits. Great place in the winter with miles of free , groomed cross-country skiing and snowshoeing trails as well.

CloverCroft - "Far from the madding crowd."
CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.

Dog friendly, lower level apartment off the "Kanc"
The cabin is located off Kancamagus Hwy, one of the most scenic roads in the US. The outdoor activities are endless, from hiking, biking, snowshoeing, alpine/x country skiing , golfing, horseback riding and tons of shopping at the infamous "outlet stores" You’ll love the cabin because of it's rustic motif, quiet neighborhood, and fresh mountain air. The cabin is good for couples, solo adventurers, biz travelers, and furry friends .

The NEST Haven awaits you.
You found your ultimate relaxation spot, sandy beaches on Rock Haven Lake (only 800' from your front door) infrared Sauna (accessible through the secret door) , 3 person hot tub, outdoor (seasonal) shower, luscious king seize bed, 6' TIPI daybed, firepit, outdoor tipi swing, a balcony and deck to enjoy the peaceful neighborhood. Round shower and deep claw foot soaker tub. Enjoy, relax and let your soul ponder.

Lake View Cottage / Fenced in Yard / Pet Friendly
Discover NH’s charm in our family-friendly cottage: Highlights: • Family and Pet-Friendly • Bright, recently renovated • Stunning lake views in a fantastic neighborhood Convenient Location: • Prime spot across from the lake • Use the boat launch for easy lake access Outdoor Adventures: • Ideal for fishing • Bring your own kayak or boat Winter Note: • Fenced yard may be inaccessible in winter.
Popular amenities for Ossipee vacation rentals
Other great vacation rentals in Ossipee

Cozy Cabin w/ Pond Access

Lakefront Boutique Cabin

New-Adorable Spacious "Garden Cape" Guest Suite

Peaceful Ossipee Lake Cottage Private Beach/Dock

Peaceful Lakefront Retreat

Peaceful 4 bedroom lakehouse retreat

Moody Farm Retreat

Ossipee Lake Waterfront Condo
When is the best time to visit Ossipee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $316 CAD | $319 CAD | $314 CAD | $316 CAD | $316 CAD | $336 CAD | $343 CAD | $371 CAD | $316 CAD | $289 CAD | $291 CAD | $316 CAD |
| 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 |
Frequently Asked Questions
What are the most popular amenities for House Rentals in Ossipee?
Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with free parking, over 70 homes with a kitchen, over 70 homes with wifi, over 60 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Ossipee have free parking?
Absolutely! We offer over 70 house rentals with free parking in Ossipee. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Ossipee?
Experience the best of Ossipee with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Where should I stay in Ossipee?
Make yourself at home in Ossipee by choosing from our most frequently booked neighborhoods. We have over 70 vacation rentals in West Ossipee, and over 70 vacation rentals in Effingham Falls.
Do cottage rentals in Ossipee have a kitchen?
Absolutely! We offer over 10 cottage rentals with a kitchen in Ossipee. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Ossipee have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Ossipee. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Ossipee?
Yes! Work meets play with ease at over 60 vacation rentals in Ossipee featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do cabin rentals in Ossipee have air conditioning?
Absolutely! We offer over 10 cabin rentals with air conditioning in Ossipee. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Ossipee?
Four-legged friends are welcome in Ossipee. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Ossipee?
Ossipee has more than 120 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about vacation rentals in Ossipee

Total vacation rentals
Explore 160 vacation rentals in Ossipee

Nightly prices starting at
Ossipee vacation rentals start at $56 CAD per night before taxes and fees

Verified guest reviews
Over 5,500 verified reviews to help you choose

Family-friendly vacation rentals
120 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
150 of Ossipee vacation 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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- Pet-friendly rentals Ossipee
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- Family-friendly rentals Ossipee
- House rentals Ossipee
- Rentals with a fireplace Ossipee
- Rentals with lake access Ossipee
- Rentals with a firepit Ossipee
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- Waterfront rentals Ossipee
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Squam Lake
- Story Land
- Scarborough Beach
- York Harbor Beach
- Weirs Beach
- Long Sands Beach
- Loon Mountain Resort
- Mount Washington Cog Railway
- Pats Peak Ski Area
- Franconia Notch State Park
- Diana's Baths
- East End Beach
- Omni Mount Washington Resort
- Dunegrass Golf Club
- Funtown Splashtown USA
- Tenney Mountain Resort
- Willard Beach
- Cannon Mountain Ski Resort
- King Pine Ski Area
- Wentworth by the Sea Country Club
- Short Sands Beach




