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Top Holiday Rentals in Ossipee

Our top choices for Ossipee holiday rentals

Condo

3.0 star property
8.0 out of 10, Very good, (2)
"I liked the accessibility to the shopping centers "
The price is £182
includes taxes & fees
26 Aug - 27 Aug
Condo

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

9.8 out of 10, Exceptional, (175)
"Fantastic stay! The house was spotless, beautifully decorated, and had all the amenities we needed for a comfortable stay. The location was perfect—close to everything yet peaceful and relaxing. The host was responsive and made the check-in process seamless. Highly recommend and would definitely stay again!"
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land

10.0 out of 10, Exceptional, (2)
"Stayed for 2 nights and had a wonderful relaxing time. Very kind and repsonsive hosts. We especially loved the fire pit. Would stay again in a heart beat. "
The price is £120
includes taxes & fees
25 Aug - 26 Aug
1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land

great location weirs beach area rental

9.4 out of 10, Exceptional, (21)
"The property was exactly as it was listed, The host was great"
The price is £337
includes taxes & fees
25 Aug - 26 Aug
great location weirs beach area rental

Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.

9.4 out of 10, Exceptional, (139)
"Everything was clean & convenient. Such a beautiful beach also! "
Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.

Stunning lakefront home with private dock, deck, firepit, and lake view

9.0 out of 10, Wonderful, (19)
"We loved the lake, the firepit and the home! Had a fun family time!"
Stunning lakefront home with private dock, deck, firepit, and lake view

Grand Blanc Mountain Home

9.6 out of 10, Exceptional, (96)
"What a treat to stay in such a magnificent home. Great fun to just look around and appreciate the scale and attention to detail that is everywhere. Great comforts and utility made our stay so enjoyable. Thank you!"
Grand Blanc Mountain Home

Walk to wedding venues, shops, dining, hiking, movies, ice cream & dog friendly.

10.0 out of 10, Exceptional, (178)
"Amazing property and great location. The host could not have been nicer- we will be back! "
Walk to wedding venues, shops, dining, hiking, movies, ice cream & dog friendly.

Cabin for two with lake views & access Now featuring AC Wi-FI and TV

9.8 out of 10, Exceptional, (11)
"Great place, quiet and immaculate~!"
The price is £142
includes taxes & fees
14 Sept - 15 Sept
Cabin for two with lake views & access Now featuring AC Wi-FI and TV

Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi

10.0 out of 10, Exceptional, (12)
"We enjoyed our time so much. My dogs roamed around and everyone was so kind and the fire pit was fantastic."
The price is £202
includes taxes & fees
25 Aug - 26 Aug
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

10.0 out of 10, Exceptional, (84)
"The property was well appointed and located right in the middle of the area where our activities were planned."
The price is £235
includes taxes & fees
26 Aug - 27 Aug
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

Cottage with Lake Views & Access Now featuring AC Wi-FI and TV

9.8 out of 10, Exceptional, (6)
"Everything was great!"
The price is £143
includes taxes & fees
9 Sept - 10 Sept
Cottage with Lake Views & Access Now featuring AC Wi-FI and TV

New Lakefront Home sleeps 14 with dock.

8.6 out of 10, Excellent, (65)
"Overall we enjoyed our stay. The house suited us just fine, no complaints. "
The price is £503
includes taxes & fees
3 Sept - 4 Sept
New Lakefront Home sleeps 14 with dock.

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

9.0 out of 10, Wonderful, (21)
"Excellent"
The price is £214
includes taxes & fees
25 Aug - 26 Aug
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

Stand alone waterfront rustic cabin!

10.0 out of 10, Exceptional, (47)
"Beautiful property, nice and quiet"
Stand alone waterfront rustic cabin!

Ideal location - Walk to Settler's Green Shops, Restaurants Pets OK.

8.0 out of 10, Very good, (38)
"Very nice place clean and in great location"
The price is £160
includes taxes & fees
2 Sept - 3 Sept
Ideal location - Walk to Settler's Green Shops, Restaurants Pets OK.

Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing

10.0 out of 10, Exceptional, (12)
"Great place to stay. Was the perfect spot to git the white mountains/conway. While also being super close to the pavilion to take in a concert. Would definitely stay here again/recommend!"
Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

8.8 out of 10, Excellent, (16)
"Nice location on the lake."
The price is £236
includes taxes & fees
25 Aug - 26 Aug
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Lakefront cottage with deck, patio, firepit, AC & W/D - secluded location

9.4 out of 10, Exceptional, (66)
"We have been staying at this property for years and love it! Cleaning was a bit spotty, but still worth the stay!"
Lakefront cottage with deck, patio, firepit, AC & W/D - secluded location

Lakefront Chalet in the White Mountains 3 bedrooms-Sleeps 5 NH. License # 044583

9.6 out of 10, Exceptional, (182)
"Excellent cottage in an even better location with astounding views"
Lakefront Chalet in the White Mountains 3 bedrooms-Sleeps 5 NH. License # 044583
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ossipee Hotel Reviews

Frequently asked questions

Can I find a holiday rental in Ossipee?

Yes, there are holiday rentals close to the most popular sights in Ossipee, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Ossipee has to offer?

Perfect Modern Lake Front Retreat with Dock! Sleeps 4: This holiday home rental outside of Ossipee is located near skiing, and offers a BBQ, air conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

How many holiday rentals are there in Ossipee?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Ossipee stay.

What’s there to see and do in Ossipee?

While exploring the area, visit family-friendly sights like Kellerhaus, or get outside and enjoy nature at Lake Winnipesaukee. In the wider area, you’ll find Ossipee Lake Trail and Lake Wentworth.

What’s a holiday rental in Ossipee like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossipee. Holiday rentals offer amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.