Ossipee Vacation Rentals from $181: Search Short-Term Rentals

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Our top choices for Ossipee vacation rentals

A garden with a white pergola, red chairs, and pink flowers.

1. Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath

Wolfeboro

Anais & Zach

$162 nightly

Oct 26 - Oct 27

Total with taxes and fees

A cabin with a picnic table and a fire pit, surrounded by large rocks and trees, overlooking a lake with boats.

2. Danforth Bay Camping and RV Resort

Freedom

Jacqui

$167 nightly

Oct 15 - Oct 16

Total with taxes and fees

3. Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard

Wolfeboro

Anonymous traveler

$160 nightly

Oct 15 - Oct 16

Total with taxes and fees

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dining table with a placemat and a bowl.

4. Cozy Tuftonboro Escape: Steps to Private Beaches!

Center Tuftonboro

Diane S.

$437 nightly

Oct 18 - Oct 19

Total with taxes and fees

A spacious kitchen with wooden beams, a large dining table, and a fireplace.

5. Cozy Tuftonboro Escape: Steps to Private Beaches!

Tuftonboro

Denise

$426 nightly

Oct 18 - Oct 19

Total with taxes and fees

A two-story house with a white front porch, a staircase, and a garage.

6. Caretakers -Split level Pet Friendly $50 Fee

Wolfeboro

Judith

$153 nightly

Oct 22 - Oct 23

Total with taxes and fees

A garden with various plants and trees, including a prominent cactus and some flowering plants.

7. 1 of 2 Cozy Cabins on Sloaping Forested Land

Shapleigh

Maja R.

$110 nightly

Oct 21 - Oct 22

Total with taxes and fees

A spacious kitchen with a large island, white cabinetry, and a view of a playground through large windows.

8. Newly Renovated Cottage 3 on Main Street Alton Bay!

Alton

David

$216 nightly

Oct 26 - Oct 27

Total with taxes and fees

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Top Ossipee Hotel Reviews

The Green Granite North Conway, an Ascend Collection Hotel

8/10 Good

"Good location. A bit dated. Friendly staff."

Fireside Inn & Suites Gilford

10/10 Excellent

"We needed a space for recovering from traveling and staying in too many places for our trip. We decided to stay here two nights and rest and relax. We also did laundry, and took a walk down to the beach for a break. We had one of the suites, with full kitchen and separate bedroom. There was a pleasant deck outside the living room and bedroom and everything was comfortable and what we needed. It felt like a vacation. We used the kitchen and heated dinners in the microwave and had breakfast in the dining space. It was a great place to stay and offered the amenities we wanted in the middle of a hectic trip."

Purity Spring Resort

8/10 Good

"We have been staying here for 30+ years. It is in an absolutely beautiful location, as scenic as it gets. Lots of boating experience on the lake, canoe and kayak. Lost of hiking trails from the property, including a nice 25 minute "mountain climb" staring directly behind the tennis courts. Overall we highly recommend it. It has many lodging options, each different from the others, and reasonably priced. At one point it was not being as well maintained, but the owners have made substantial improvements in the past two years. By way of constructive criticism - the dining services. The dining room is very nicely appointed. But in recent years there has not been a serious commitment to the food services. The breakfast menu is a fraction of what it used to be, and is very limited. The owners should either make a more serious commitment to providing better food services on campus, or stop providing them altogether."

Snowvillage Inn

10/10 Excellent

"The location was off the beaten path and in the woods. Quiet cozy room ( no TV ) price was more than reasonable considering what hotels on the Conway strip cost. Free breakfast was simple, apples,oranges, muffins, pastries, coffee, tea. Stayed for Fryburg Fair.20 minutes away. Hot water in the morning was an issue as it was only lukewarm both shower and sink . Wall heater in bathroom didn’t work but wasn’t needed ( 35 degrees outside). Electric heat worked . These issues I’ve had in major Hotels . Rooms at Marriott, Hilton, no name motels were 2+ times higher in price the same time we stayed for the Fair. The hot water did work when we first arrived as my wife took her shower but not in the morning.."

Find out more about Ossipee

Everything you need to know about Ossipee vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ossipee vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ossipee vacation 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 low season months. For more hustle and bustle, you may prefer to visit Ossipee in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $181 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ossipee rentals

At Expedia, we put the best Ossipee vacation 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 vacation.

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 vacation rental in Ossipee?

Yes, we offer vacation rentals close to the most popular points of interest in Ossipee, or you can go with a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Ossipee?

Stunning Waterfront Home with Boat Dock, swim, boating. Bike & skiing nearby.: This vacation home rental outside of Ossipee is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Ossipee?

With 7 Expedia vacation rentals, you're sure 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 Libby Museum, or get outside and enjoy nature at Duncan Lake. In the larger area, you’ll find Ossipee Lake Trail and Lake Wentworth.

What’s a vacation rental in Ossipee like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Ossipee. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for family gatherings.

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Our top choices for Ossipee vacation rentals

1. Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath

2. Danforth Bay Camping and RV Resort

3. Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard

4. Cozy Tuftonboro Escape: Steps to Private Beaches!

5. Cozy Tuftonboro Escape: Steps to Private Beaches!

6. Caretakers -Split level Pet Friendly $50 Fee

7. 1 of 2 Cozy Cabins on Sloaping Forested Land

8. Newly Renovated Cottage 3 on Main Street Alton Bay!

9. A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!

10. Newly Renovated Cottage 4 in Alton Bay, NH

11. Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath

12. Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard

13. Gilford Perfect Getaway Pool, WIFI & Free Parking

14. Cottage 11 - Year Round - Pet Friendly $50 Fee- 1 Bed / 1 Bath w/ Courtyard

15. Lake Winnipesaukee Home for Fall & Winter Fun

16. Hiking & Snowmobile Trails On-Site: Alton Retreat!

17. Reconnect with Nature at this Glamping Tent in East Wakefield, New Hampshire

18. Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath

19. Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8

20. Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Find vacation rentals that suit your style

Top Ossipee Hotel Reviews

The Green Granite North Conway, an Ascend Collection Hotel

The Naswa Resort

TownePlace Suites by Marriott Gilford

Fireside Inn & Suites Gilford

Lake Wentworth Inn

Purity Spring Resort

Best Western Plus Landmark Inn

Snowvillage Inn

Weirs Beach Motel and Cottages

Find out more about Ossipee

Frequently asked questions

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