
Holiday rentals in Ossipee
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Top-rated holiday rentals in Ossipee
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Other great holiday rentals in Ossipee

Home in Wolfeboro
4.88 out of 5 average rating, 204 reviewsMountain Views & Animals near Winnipesaukee!
PatrickRating, 5 stars3 months ago
After two years away from here, the kids requested we come back. The goats, alpacas, chickens and sheep along with the surprise of puppies is always exciting. We stayed through a winter storm with snow, sleet, and high wind. Justin kept the driveway open and communicated what to do if weather turned worse. Love the old house and grounds! Thanks for having us!
Top guest favourite

Home in Tamworth
5 out of 5 average rating, 14 reviewsGames•Roku•Essentials•Firepit•<1mile to White Lake
TarunRating, 5 stars5 days ago
Had a great stay at Taylor’s place. It is built for short term as well as long term stay. He has used really great quality stuff which makes you feel like home. Kitchenware were new and best in class. On-site Laundary was really great. He has taken care of every minor details to make you feel special. We will definitely recommend.
Guest favourite

Home in Ossipee
5 out of 5 average rating, 10 reviewsThe Tinker Bell on Ossipee Lake
WadeRating, 5 stars3 weeks ago
Matt's place is an ideal location for anyone looking for a private lakeside getaway. The cabin sits on the shores of the lake and is a quick walk to a lakeside beach with mountain views. Lots of amenities and water activities available. The house was clean and large enough to comfortably host a bigger group. Grille and the pool table were nice touches. The house has a great lakeside vibe with a fireplace and plenty of wood accents. My only criticism is of the condition of the pool table and one of the cheap plastic chairs on the deck was broken. Worth the visit for the location. This is in an HOA and there are nosy neighbors, but be respectful and you'll be grand. Thanks Matt!
Guest favourite

Home in Tuftonboro
5 out of 5 average rating, 11 reviewsPeaceful Lakefront Retreat
PJRating, 5 stars1 month ago
Erin's place was the best Airbnb place I've stayed in since I became a member over 10 years ago! I cannot say enough wonderful things about it honestly, from the most comfortable bed imaginable (I took a picture of the mattress and pillows and bought them!) to the kitchen amenities and the most GORGEOUS views! I went there as a retreat from hectic Boston life and it was so peaceful I was ready to book another stay soon!
Guest favourite

Cottage in Ossipee
5 out of 5 average rating, 5 reviewsLakefront Cottage!
DeniseRating, 5 stars10 months ago
Wow, what a perfect house. Our favorite ABNB yet!! Some hi lights enjoyed by all 6 guests include comfy beds, room darkening shades, 3 full baths, coffee/drink area separate from kitchen. It was our 1st time to lake Ossipee, but it will not be our last! We swam, kayaked, fished etc. the lake was so clear and clean and warm. The scenery was spectacular. Robert was a great host and we would absolutely rent again.
Guest favourite

Tiny home in Tamworth
4.92 out of 5 average rating, 49 reviewsThe River Nook - Tiny Cozy Boho Home
LauraRating, 5 stars2 weeks ago
We had a lovely time at Katrin’s place. The property was beautiful and the tiny home was great.
Top guest favourite

Guest house in Wolfeboro
4.98 out of 5 average rating, 55 reviewsLuxury Beachfront Cottage - Perfect summer getaway
MaureenRating, 5 stars8 months ago
This beautiful cottage is such a great getaway! The grounds and lake are really beautiful. The cottage is so well done with the furnishings, quality and great use of space. Bed, linens and towels are wonderful! Also very clean! The outside kitchen within the screened area is very well appointed and furnished. I really enjoyed sitting in there at night. The cabana is such a fun sitting spot. Having all of this space and freedom to walk around the grounds was wonderful! So peaceful and their gardens are beautiful. I hope to return!!!
Superhost

Cottage in Ossipee
4.75 out of 5 average rating, 53 reviewsHear the stream from bed.
KathleenRating, 5 stars6 months ago
Very happy with our mini vaca. Haven't rented a place in a very long time so I tend to be pretty cheap lol. We had a great relaxing trip. Loved seeing the snow on Thanksgiving !! We didn't travel anywhere besides the market for one trip. We did take a short hike with our dog but he got a little too cold so we returned back to warm up!! Would definitely recommend very calming and peaceful to watch the stream was able to get some great photos!!!
Quick stats about holiday rentals in Ossipee
Total rentals
150 properties
Nightly prices starting at
$51 SGD before taxes and fees
Total number of reviews
5.7K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
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- Cottage rentals Ossipee
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Squam Lake
- Scarborough Beach
- York Harbor Beach
- Story Land
- Loon Mountain Resort
- Attitash Mountain Resort
- Weirs Beach
- Owl's Nest Resort
- Long Beach
- Surfside Beach
- Long Sands Beach
- Franconia Notch State Park
- Pats Peak Ski Area
- Bear Brook State Park
- Wentworth by the Sea Country Club
- Mount Washington Cog Railway
- East End Beach
- Cranmore Mountain Resort
- Cannon Mountain Ski Resort
- Palace Playland
- Ferry Beach