Ossipee Holiday Rentals

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Check prices for these dates

Tonight
16 Jul - 17 Jul
Tomorrow
17 Jul - 18 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in Ossipee

Condo
Living area

Condo

2.5 star property
Condo
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Relax on the lakeside deck with a tranquil view of the water and distant hills.

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

9.6 out of 10, Exceptional, (19)
"The place was quaint, modern and lovely. The views were fabulous! "
The price is HK$2,033
HK$3,250 total
includes taxes & fees
17 Jul - 18 Jul
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Cabin for two with lake views & access Now featuring AC Wi-FI and TV
Stunning waterfront views of a bustling marina with a large cruise ship and various boats.

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

9.8 out of 10, Exceptional, (8)
"Great place, quiet and immaculate~!"
The price is HK$1,154
HK$1,924 total
includes taxes & fees
31 Jul - 1 Aug
Cabin for two with lake views & access Now featuring AC Wi-FI and TV
Lakefront cottage with deck, patio, firepit, AC & W/D - secluded location
Enjoy cooking in the well-equipped kitchen with a stove, oven, and ample counter space.

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

9.4 out of 10, Exceptional, (65)
"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
1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land
Surrounded by lush vegetation, this serene garden offers a peaceful escape.

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

The price is HK$981
HK$1,241 total
includes taxes & fees
20 Jul - 21 Jul
1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land
Ideal location - Walk to Settler's Green Shops, Restaurants Pets OK.
Kitchen features a stove, microwave, sink, and kettle.

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

8.0 out of 10, Very good, (36)
"Very nice place clean and in great location"
The price is HK$777
HK$1,695 total
includes taxes & fees
4 Aug - 5 Aug
Ideal location - Walk to Settler's Green Shops, Restaurants Pets OK.
Leaward Shores Guesthouse | Lake view home in Moultonborough with dock & deck
Enjoy a serene waterfront retreat with a spacious balcony and dock.

Leaward Shores Guesthouse | Lake view home in Moultonborough with dock & deck

10.0 out of 10, Exceptional, (8)
"Perfect location for us, simple and easy."
Leaward Shores Guesthouse | Lake view home in Moultonborough with dock & deck
Beach House on the Big Lake with 90-foot dock. Bring your boat! New listing!
Exterior

Beach House on the Big Lake with 90-foot dock. Bring your boat! New listing!

Beach House on the Big Lake with 90-foot dock. Bring your boat! New listing!
Stand alone waterfront rustic cabin!
Escape to a serene lakeside haven surrounded by lush foliage and calm waters.

Stand alone waterfront rustic cabin!

10.0 out of 10, Exceptional, (46)
"Beautiful property, nice and quiet"
Stand alone waterfront rustic cabin!
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Swimmers can enjoy the pool surrounded by wooden beams and clear lane dividers.

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

10.0 out of 10, Exceptional, (174)
"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!"
The price is HK$12,387
HK$22,128 total
includes taxes & fees
17 Jul - 18 Jul
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Chestnut Cove Cottage- Winnipesaukee - Alton
Fridge, microwave, oven, stovetop

Chestnut Cove Cottage- Winnipesaukee - Alton

Chestnut Cove Cottage- Winnipesaukee - Alton
Lakefront home with views, water access for boating & swimming
Relax on the porch with comfortable seating and a scenic view.

Lakefront home with views, water access for boating & swimming

8.6 out of 10, Excellent, (39)
"We booked a weekend getaway and our stay was very pleasant. It was an older cottage and some updating is needed but it had a very cozy feel. The fire pit and listening to the choppy water was very relaxing. The highlight of the trip was the views. Omg was it so breathtaking. Would definitely book again. "
Lakefront home with views, water access for boating & swimming
Stunning lakefront gem with full water view, beach access & dock
Relax in this cabin with a comfortable sofa, two wicker rocking chairs, and a large window offering a forest view.

Stunning lakefront gem with full water view, beach access & dock

10.0 out of 10, Exceptional, (9)
"A perfect little cottage for a getaway for two, to the lake. Great experience and would happily return someday."
Stunning lakefront gem with full water view, beach access & dock
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin
Compact kitchen with a stove, microwave, and sink, offering a convenient space for meal preparation.

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

10.0 out of 10, Exceptional, (81)
"The property was well appointed and located right in the middle of the area where our activities were planned."
The price is HK$1,405
HK$2,427 total
includes taxes & fees
21 Jul - 22 Jul
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin
Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni
Relax by the serene lake with a tranquil view of distant mountains, surrounded by a grassy area, picnic tables, and a shaded seating area.

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

9.6 out of 10, Exceptional, (138)
"Everything was clean & convenient. Such a beautiful beach also! "
Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
Overlooking the marina, this property offers stunning views of the ocean and surrounding hills.

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

10.0 out of 10, Exceptional, (8)
"We enjoyed our time so much. My dogs roamed around and everyone was so kind and the fire pit was fantastic."
The price is HK$1,303
HK$2,591 total
includes taxes & fees
17 Jul - 18 Jul
Lake View Cabin in Alton Bay Now featuring Lake Access, AC/ TV/ WiFi
Adorable Cabin with stunning lake views & Now featuring AC Wi-FI and TV access
Relax on the serene lakeside beach with a view of the water's edge.

Adorable Cabin with stunning lake views & Now featuring AC Wi-FI and TV access

9.2 out of 10, Wonderful, (5)
"We had an amazing stay, adorable area, loved the access to the lake and kayaking, close to great options for outdoor place. Looking forward to future trips"
The price is HK$1,005
HK$1,736 total
includes taxes & fees
17 Jul - 18 Jul
Adorable Cabin with stunning lake views & Now featuring AC Wi-FI and TV access
Lake Winnipesaukee Island Retreat Sandy Beach
Fridge, oven, stovetop, coffee/tea maker

Lake Winnipesaukee Island Retreat Sandy Beach

Lake Winnipesaukee Island Retreat Sandy Beach
Waterfront cabin near Fish Cove with private dock, water access, firepit, grill
Enjoy meals in the kitchen with an oven and toaster, surrounded by a large dining table and comfortable chairs.

Waterfront cabin near Fish Cove with private dock, water access, firepit, grill

9.2 out of 10, Wonderful, (15)
"My family and I had a great time at this home. Perfect location, nice quiet cove on the lake, we'd definitely stay again!"
Waterfront cabin near Fish Cove with private dock, water access, firepit, grill
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room
Relax in a serene hot tub surrounded by a deck with a white railing.

Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room

9.8 out of 10, Exceptional, (164)
"We were visiting NH for only a day and was lucky enough to stumble upon this place! The host was very communicative, and everything was top notch! Very close to many mountains. Food locally was AMAZING. The hot tub and game room were great. HIGHLY RECOMMEND!"
The price is HK$1,766
HK$3,654 total
includes taxes & fees
20 Jul - 21 Jul
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room
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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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 kitchenware.

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.