Ossipee Holiday Rentals

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Holiday Rentals in Ossipee

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

10.0 out of 10, Exceptional, (157)
"The location is exceptional. The pool area, steam room, sauna, and total recreation area were amazing. The pool temperature (air and water) was good for this time of year. The consistent 4 foot pool depth made it great for a community water volley ball game. (*We are all over 65) Having 5 "king bedrooms with three bathrooms in three different areas of the house allowed the entire adult group comfort and privacy. We also made use of the 2 bathrooms near the pool. The extra large living...
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

Spacious Belmont Home w/ Seasonal Pool & Grill!

9.0 out of 10, Wonderful, (65)
"We had an amazing experience here! From booking to check-in to the weekend stay, everything was smooth and easy. Robert was excellent with answering questions, allowing an early check-in and an extended checkout, and was very responsive with communication. I met property managers Brandon, Jared, and Craig when I arrived and they were super helpful (and gave a great pizza delivery recommendation)! The house was exactly as advertised. Plenty of space for our group, clean and organized, and...
Spacious Belmont Home w/ Seasonal Pool & Grill!

Pet-friendly Waterfront Cottage: On-site Bunkhouse

3.0 star property
Pet-friendly Waterfront Cottage: On-site Bunkhouse

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (23)
"Beautiful home. Great weekend away!! "
Cozy, Pet-Friendly Escape Near Lake & Mountains

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

8.8 out of 10, Excellent, (15)
"We stay. In Alton Bay each year for a couple of concerts at Bank of NH Pavilion in Gilford. We extend it by staying for a couple of days at Lake Winnipesaukee The motel is perfectly located close to the venue and on the lake for swimming and boating while visiting BNH Pavilion. The motel is in a pine grove and is lake front. It's "!old school " feel reminds of my childhood. It's clean and quite, but no thrills. Don't expect first class accommodations but if you like the feel of a...
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

8.6 out of 10, Excellent, (24)
"Nice home, close to bank of NH pavilion, and Weirs beach. "
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach

4Bedrm Sleeps 12 Winnipesaukee Waterfront gradual sandy sloped shoreline Pets OK

9.0 out of 10, Wonderful, (8)
"The house was clean and comfortable. It was roomy. The views were great. The owners were helpful and friendly. We would stay here again. "
4Bedrm Sleeps 12 Winnipesaukee Waterfront gradual sandy sloped shoreline Pets OK

Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome

10.0 out of 10, Exceptional, (160)
"Wouldn’t change a thing! The house was wonderful and Sharon was amazing. Had a great vacation and would definitely stay here again."
Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome

Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

10.0 out of 10, Exceptional, (7)
"Great location, beautiful house , we were a bit upset that the outside hot tub was not available even though it was listed as part of the amenities."
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

Secluded, dog-friendly home with screened porch, firepit, fireplace & W/D

6.8 out of 10, (9)
"I didn’t look close at the on-line pics so at first arrival I had concerns. It’s a charming older style lake house that could use a bit of pampering but it was very clean and comfortable for our group of 8. The host and management company were great and easy to communicate with. We came up for our daughter’s wedding and we all had a very nice weekend. Thank you"
Secluded, dog-friendly home with screened porch, firepit, fireplace & W/D

Pet Friendly, Quiet Neighborhood, Cozy lower level cabin

9.8 out of 10, Exceptional, (76)
"Very spacious and cozy cabin! Marianne was very accommodating. She responded very quickly to all emails. The cabin was very clean. We would love to stay again when we're in the Conway area."
The price is AU$415
includes taxes & fees
25 Nov - 26 Nov
Pet Friendly, Quiet Neighborhood, Cozy lower level cabin

Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet

8.8 out of 10, Excellent, (19)
"Great time."
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet

Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

10.0 out of 10, Exceptional, (86)
"Hanna was a wonderful host! When we had an issue with water pressure in the shower, she responded within minutes and had someone out to fix it within about an hour. The place is rustic but charming with a great fireplace!"
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

Lakefront studio with private dock, fast WiFi & full kitchen - dog-friendly

9.8 out of 10, Exceptional, (28)
"Great spacious "studio" in a super quiet neighborhood. The bed was so comfy, the kitchen immaculate and to die for! I was lucky to have great weather where I was able to leave all the sliders wide open day and night. Good size for even a family with 2 small children."
Lakefront studio with private dock, fast WiFi & full kitchen - dog-friendly

The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV

9.8 out of 10, Exceptional, (7)
"Nice location close to Alton Bay. The Hideaway #10 was comfortable and well appointed. A bit more attention to the bedroom, kitchen and grill cleanliness would make it perfect."
The Hideaway, lake views & access sleeps 8 Now featuring AC Wi-FI and TV

Condo with WiFi, private beach, full kitchen, & outdoor pool

7.8 out of 10, Good, (36)
"Great for a younger couple wanting a bargain spot close to the many local attractions."
Condo with WiFi, private beach, full kitchen, & outdoor pool

Amazing lakefront retreat with stunning views - near skiing & golf

7.8 out of 10, Good, (9)
"Mediocre Couldnt turn on ceiling fans AC was inadequate Use of fireplace is forbidden Asked for light bulbs but never received "
Amazing lakefront retreat with stunning views - near skiing & golf

Private Beachfront Family Retreat On Lake Winnipesaukee - Amazing Long Views

9.2 out of 10, Wonderful, (53)
"We came up to the house for a few days in October. Weather was beautiful - Lakeview nothing but stunning. The house is very charming. The old NH lakehouse vibes are tangible at all times. Very clean, very well equipped. As the nights were at freezing temperature we appreciated that the house always felt warm and cozy. Amazing place to stay with an extended family."
Private Beachfront Family Retreat On Lake Winnipesaukee - Amazing Long Views

Lakefront four season home w/private beach, boat slip, dock, & fishing kayaks

9.0 out of 10, Wonderful, (24)
"The view was beautiful and had a dock for the boat. With a propane fire pit & nice grill! The beds were AWFUL. We were better off sleeping on the floor. Lots of ants, they got in some of our food, furniture in living room is more for show- also uncomfortable. As long as you’re staying outside it’s a great stay!"
Lakefront four season home w/private beach, boat slip, dock, & fishing kayaks

Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach

9.4 out of 10, Exceptional, (74)
"We liked our experience at this cabin and it allowed us to do great activities in the White mountains (my spouse, myself and our dog). The cabin is super cozy and confortable with the heating and AC units. However, we noted 3 downsides that can't give the 5 star review : - General cleanliness was okay, but not great. A good portion of the dishes and cookware were pretty dirty and we had to do a lot of dishes upon arrival. - We wanted to use the kayaks on the lake, but we were just not able to...
Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach
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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Other types of properties in Ossipee you may be interested in

Green Granite Inn, Ascend Hotel Collection

2.5 star property
7.2 out of 10, Good, (1226)
"Everything you need is at this hotel for a reasonable price "
The price is AU$85
includes taxes & fees
26 Nov - 27 Nov
Green Granite Inn, Ascend Hotel Collection

Home2 Suites by Hilton North Conway

3.0 star property
9.6 out of 10, Exceptional, (447)
"We had a great stay! The hotel was clean, comfortable, and the staff was helpful and friendly. The location was great too!"
The price is AU$183
includes taxes & fees
1 Dec - 2 Dec
Home2 Suites by Hilton North Conway

Quality Inn

2.5 star property
7.6 out of 10, Good, (933)
"One of our three day stops, great location and well maintained. It’s been our 4th stay in last 8 years, never disappointed."
The price is AU$105
includes taxes & fees
10 Dec - 11 Dec
Quality Inn
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski: This holiday home rental outside of Ossipee is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Funspot Family Fun Center, or get outside and enjoy nature at Lake Wentworth. In the wider area, you’ll find Ossipee Lake and Great East Lake.

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.