Ossipee Holiday Rentals

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Our top choices for Ossipee holiday rentals

Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon
Lebanon
10.0 out of 10, Exceptional, (25 reviews)
"Everything about our stay was lovely! Check-in was smooth, the property was gorgeous, and the cottage was full of charm. "
United States
Daniel S.
The price is AU$330
includes taxes & fees
9 Apr - 10 Apr
Rustic Rose Cottage of Historic West Lebanon

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.6 out of 10, Exceptional, (11 reviews)
"Excellent stay"
United States
Kara
The price is AU$257
includes taxes & fees
9 Apr - 10 Apr
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Wolfeboro
10.0 out of 10, Exceptional, (17 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is AU$259
includes taxes & fees
9 Apr - 10 Apr
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Rufus III Yurt on the river

Rufus III Yurt on the river
Brownfield
10.0 out of 10, Exceptional, (12 reviews)
"Had a great time,will be back for sure. "
United States
John C.
The price is AU$271
includes taxes & fees
10 Apr - 11 Apr
Rufus III Yurt on the river

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

1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land
Shapleigh
9.0 out of 10, Wonderful, (4 reviews)
"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. "
United States
Bethany K.
The price is AU$227
includes taxes & fees
1 May - 2 May
1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land

Lotus Spa, your home away from home

Lotus Spa, your home away from home
Acton
10.0 out of 10, Exceptional, (50 reviews)
"This place has thought of absolutely everything to make it a cozy and relaxing stay "
United States
Cara L.
The price is AU$447
includes taxes & fees
14 Apr - 15 Apr
Lotus Spa, your home away from home

Stunning Lake Views close to Weirs Beach & Gunstock

Stunning Lake Views close to Weirs Beach & Gunstock
Weirs Beach
The price is AU$299
includes taxes & fees
9 Apr - 10 Apr
Stunning Lake Views close to Weirs Beach & Gunstock

Ava Jade yurt nestled in the woods of Brownfield, Maine

Ava Jade yurt nestled in the woods of Brownfield, Maine
Brownfield
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful , clean , secluded Yurt . We truly enjoyed our stay "
United States
Judy S.
The price is AU$239
includes taxes & fees
10 Apr - 11 Apr
Ava Jade yurt nestled in the woods of Brownfield, Maine

Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Wolfeboro
10.0 out of 10, Exceptional, (18 reviews)
"We had the best time here, would 100% go back. Very quiet and relaxing and the hosts were great."
United States
The F.
The price is AU$880
includes taxes & fees
9 Apr - 10 Apr
Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Meredith Bay - Brand New 1st Floor Apartment In Private Home

Meredith Bay - Brand New 1st Floor Apartment In Private Home
Meredith
9.8 out of 10, Exceptional, (47 reviews)
"Very clean and very comfortable. Short walk to downtown made our stay perfect. "
United States
Julian G.
The price is AU$417
includes taxes & fees
9 Apr - 10 Apr
Meredith Bay - Brand New 1st Floor Apartment In Private Home

Waterfront w/ Prvt Dock & Firepit | Sleeps 8

Waterfront w/ Prvt Dock & Firepit | Sleeps 8
Acton
9.6 out of 10, Exceptional, (15 reviews)
"Love the area & location on the lake!"
United States
Will M.
The price is AU$818
includes taxes & fees
9 Apr - 10 Apr
Waterfront w/ Prvt Dock & Firepit | Sleeps 8

Cozy three bedroom house located just five minutes from Lake Winnipesaukee

Cozy three bedroom house located just five minutes from Lake Winnipesaukee
Wolfeboro
8.0 out of 10, Very good, (17 reviews)
"Thanks for a great stay!"
United States
Lynne Q.
The price is AU$503
includes taxes & fees
9 Apr - 10 Apr
Cozy three bedroom house located just five minutes from Lake Winnipesaukee

Inviting condo in quiet locale with partial lake views, balcony & grilling area

Inviting condo in quiet locale with partial lake views, balcony & grilling area
Gilford
8.4 out of 10, Very good, (17 reviews)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
The price is AU$385
includes taxes & fees
9 Apr - 10 Apr
Inviting condo in quiet locale with partial lake views, balcony & grilling area

Great Conway Location! Shop Eat Hike Swim

Great Conway Location! Shop Eat Hike Swim
Settlers Green
7.8 out of 10, Good, (26 reviews)
"Room was clean enough, but the location in the midst of a outlet mall left a lot to be desired for a stop on a leaf peeping vacation."
United States
Kelly C.
The price is AU$321
includes taxes & fees
9 Apr - 10 Apr
Great Conway Location! Shop Eat Hike Swim

White Mountains Waterfront Chalet w/ Private Beach

White Mountains Waterfront Chalet w/ Private Beach
Eidelweiss Village
9.8 out of 10, Exceptional, (25 reviews)
"House was cozy, well appointed, spotlessly clean and just as advertised on the site. We had a wonderful visit and would love to visit again."
United States
Tracy K.
The price is AU$619
includes taxes & fees
9 Apr - 10 Apr
White Mountains Waterfront Chalet w/ Private Beach

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin
Conway
10.0 out of 10, Exceptional, (95 reviews)
"The notes are helpful. Easy check in and out. The house is clean and cozy."
United States
Tessie
The price is AU$352
includes taxes & fees
13 Apr - 14 Apr
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home

Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home
Meredith
10.0 out of 10, Exceptional, (171 reviews)
"We loved our stay. Very clean and in a great location in Meredith."
United States
Rebecca R.
The price is AU$444
includes taxes & fees
9 Apr - 10 Apr
Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Alton
9.4 out of 10, Exceptional, (25 reviews)
"Great visit and property as described! Clean, all inclusive, and would recommend. View was beautiful and had a wonderful time."
United States
Catherine M.
The price is AU$526
includes taxes & fees
21 Apr - 22 Apr
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

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

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Alton
9.0 out of 10, Wonderful, (22 reviews)
"Great little gem given its price, location, and overall accommodations! "
United States
Kevin R.
The price is AU$413
includes taxes & fees
8 May - 9 May
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

Artsy Woodland Group Hideaway Cabin!

Artsy Woodland Group Hideaway Cabin!
Parsonsfield
8.4 out of 10, Very good, (6 reviews)
"It's not the most modern place but it is a good value, has what you need and is in a beautiful setting "
United States
Dan F.
The price is AU$754
includes taxes & fees
9 Apr - 10 Apr
Artsy Woodland Group Hideaway Cabin!
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

Find out more about Ossipee

Everything you need to know about Ossipee holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ossipee holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ossipee holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Ossipee holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossipee. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ossipee holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ossipee holiday rentals we have selected for you start as low as AU$699 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Ossipee rentals

At Expedia, we put the best Ossipee holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ossipee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ossipee holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossipee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Waterfront cabin near Fish Cove with private dock, water access, firepit, grill: This holiday home rental outside of Ossipee is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

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.