An aerial view of a lakeside town with colorful autumn foliage, a church, and a marina with boats.

Wolfeboro Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Wolfeboro holiday rentals

A serene lakeside view at sunset with a silhouette of trees and a calm water surface.

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

Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
Wolfeboro
9.8 out of 10, Exceptional, (22 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is HK$1,196
HK$1,485 total
includes taxes & fees
25 Oct - 26 Oct
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A two-story house with a white front porch, a staircase, and a garage.

2. Caretakers -Split level Pet Friendly $50 Fee

Caretakers -Split level Pet Friendly $50 Fee
Wolfeboro
10.0 out of 10, Exceptional, (5 reviews)
"I would stay there again. The caretakers place was just adorable. My stay was very relaxing and the place offered so many activities for children and adults. "
United States
Judith
The price is HK$1,045
HK$1,304 total
includes taxes & fees
7 Oct - 8 Oct
Caretakers -Split level Pet Friendly $50 Fee
A garden with a white pergola, red chairs, and pink flowers.

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

Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.4 out of 10, Exceptional, (13 reviews)
"Great place "
United States
Anonymous traveller
The price is HK$1,111
HK$1,384 total
includes taxes & fees
25 Oct - 26 Oct
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
A two-story house with a dark roof, multiple windows, and a porch with chairs.

4. Downtown Wolfeboro condo, right on Wolfeboro Bay/Winnipesaukee w/dock available

Downtown Wolfeboro condo, right on Wolfeboro Bay/Winnipesaukee w/dock available
Wolfeboro
7.2 out of 10, Good, (5 reviews)
"No way does this deserve a 10/10 rating. It’s fairly terrible and not deserving such a favorable rating. The pluses - great location, right on the lake. Adirondacks at sunset was heavenly. Super convenient. Wolfeboro is very cute. The shower has been nicely redone. The in-unit washer/dryer worked well and was very convenient. But the negatives are many. Lots of disrepair and terrible attention to detail. We got a spongy soft double bed. The listing says Queen bed. It’s not. We had badly stained...
United States
Brian L.
The price is HK$1,114
HK$2,307 total
includes taxes & fees
2 Nov - 3 Nov
Downtown Wolfeboro condo, right on Wolfeboro Bay/Winnipesaukee w/dock available
A modern kitchen with white cabinets, a built-in microwave, and a dishwasher. There are two bar stools near the kitchen counter.

5. 9 Lake Street

9 Lake Street
3.0 star property
Wolfeboro
8.0 out of 10, Very good, (2 reviews)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is HK$1,860
HK$2,899 total
includes taxes & fees
12 Oct - 13 Oct
9 Lake Street
A two-story building with a balcony, outdoor seating, and a sign for 'Market21.'

6. Cozy 1BR Getaway Steps from Lake Winnipesaukee

Cozy 1BR Getaway Steps from Lake Winnipesaukee
Wolfeboro
7.6 out of 10, Good, (4 reviews)
"I am a travel nurse so was great location for me for a few weeks."
United States
Lori C.
The price is HK$1,617
HK$2,830 total
includes taxes & fees
12 Oct - 13 Oct
Cozy 1BR Getaway Steps from Lake Winnipesaukee
A garden with a white pergola, red chairs, and pink flowers.

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

Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (6 reviews)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
The price is HK$1,111
HK$1,385 total
includes taxes & fees
2 Nov - 3 Nov
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
A house with a porch, surrounded by a garden with pink and yellow flowers.

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

Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
Wolfeboro
9.0 out of 10, Wonderful, (7 reviews)
"Great location & comfortable! "
United States
Jeanine L.
The price is HK$1,083
HK$1,345 total
includes taxes & fees
22 Oct - 23 Oct
Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
A waterfront area with a large white building, a dock with boats, and a clock tower in the background.

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

Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (5 reviews)
"We had a perfect stay. Super cute cabin, clean and very comfortable.We thoroughly enjoyed or time there. Very easy process and would absolutely recommend and book again."
United States
Jessica G.
The price is HK$1,252
HK$1,555 total
includes taxes & fees
3 Nov - 4 Nov
Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
A sunset over a calm lake with trees silhouetted against the sky.

10. Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath

Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath
Wolfeboro
9.6 out of 10, Exceptional, (4 reviews)
"In addition to everything this property offers we found there was a nearby 12mile bike trail that goes through the woods passing lakes on the the route, and bikes were available at the property."
United States
Justin
The price is HK$1,648
HK$2,043 total
includes taxes & fees
20 Oct - 21 Oct
Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath
A garden with a white pergola, red chairs, and pink flowers.

11. Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath

Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4 reviews)
"Everything was great!"
United States
Leah F.
The price is HK$1,742
HK$2,163 total
includes taxes & fees
13 Oct - 14 Oct
Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath
A modern kitchen with white cabinets, a microwave, and a stove.

12. Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Alton
10.0 out of 10, Exceptional, (1 review)
"This is a classic old-style cabin that reminded us of our childhood family trips in the 60’s. It’s not new, but a heck of a lot of fun if you’re in the right head space. Easily walked to town for dinner and to the shore. Clean and had everything we needed."
United States
Christine F.
The price is HK$872
HK$1,814 total
includes taxes & fees
7 Oct - 8 Oct
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
A coastal town with a marina, a large cruise ship docked, and a beach.

13. Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3

Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3
Alton
8.8 out of 10, Excellent, (14 reviews)
"Nicely kept enjoyable stay"
United States
Shirley G.
The price is HK$863
HK$1,812 total
includes taxes & fees
7 Oct - 8 Oct
Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3
A cozy room with a wicker sofa, a wooden ladder shelf, and a large wooden-framed window.

14. Newly Renovated Cottage 4 in Alton Bay, NH

Newly Renovated Cottage 4 in Alton Bay, NH
Alton
9.0 out of 10, Wonderful, (4 reviews)
"Communication was amazing, check in was a delightful, the house itself was perfect "
United States
Jennifer S.
The price is HK$910
HK$2,804 total
includes taxes & fees
27 Oct - 28 Oct
Newly Renovated Cottage 4 in Alton Bay, NH
A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dining table with a placemat and a bowl.

15. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
Center Tuftonboro
10.0 out of 10, Exceptional, (16 reviews)
"Property was just as pictured. Great location near the pond. Home had everything I could have needed, including a few snacks. Bit of a snafu on check-in but host communication was quick and pleasant!"
United States
Diane S.
The price is HK$1,295
HK$3,721 total
includes taxes & fees
8 Oct - 9 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!
A spacious kitchen with wooden beams, a large dining table, and a fireplace.

16. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
3.0 star property
Tuftonboro
10.0 out of 10, Exceptional, (2 reviews)
"We’ll kept "
United States
Denise
The price is HK$1,664
HK$3,628 total
includes taxes & fees
27 Oct - 28 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!
A beach with picnic tables and lounge chairs, a stone wall, and a view of the lake and distant mountains.

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

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Gilford
9.8 out of 10, Exceptional, (35 reviews)
"Great location, specially for concerts or enjoying the beach. Some road noise."
United States
Estuardo
The price is HK$1,091
HK$2,171 total
includes taxes & fees
3 Nov - 4 Nov
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
A cozy cabin interior with a sectional sofa, a leather ottoman, and a television mounted on the wall.

18. Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...

Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
Alton
10.0 out of 10, Exceptional, (5 reviews)
"Best communication ever at a VRBO. When I come back, I’m there!"
United States
shaun d.
The price is HK$1,452
HK$3,235 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
A living room with a stone fireplace, a ceiling fan, and a large window.

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

Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
Gilford
10.0 out of 10, Exceptional, (1 review)
"Home was clean Host was easy to communicate with"
United States
Robert L.
The price is HK$918
HK$3,287 total
includes taxes & fees
2 Nov - 3 Nov
Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
A large, modern building with multiple floors and a flat roof, surrounded by a snowy landscape and a body of water in the background.

20. Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!

Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!
Weirs Beach
9.2 out of 10, Wonderful, (7 reviews)
"Property was very clean, had very comfortable beds and a wonderful view. "
United States
Crystal
The price is HK$691
HK$1,702 total
includes taxes & fees
28 Oct - 29 Oct
Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!
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 Wolfeboro Hotel Reviews

Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

10/10 Excellent
"Awesome"
BETZI 1-night trip
Posted 5 hours ago
Best Western Plus Landmark Inn

Find out more about Wolfeboro

Search for holiday rentals in Wolfeboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Wolfeboro using one of the methods below:

  • View our selection of featured holiday rentals in Wolfeboro
  • Use the map to find apartments and other holiday homes in the Wolfeboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wolfeboro while they last

Look no further and take a look at our great range of rental properties in Wolfeboro!

Frequently asked questions

Are there holiday rentals in Wolfeboro?

Yes, there are holiday rentals in Wolfeboro close to Libby Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Wolfeboro speak positively about the lakeside and bars in this destination. Make sure you have time to check out the parks and museums during your trip.

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

Stunning Waterfront Home with Boat Dock, swim, boating. Bike & skiing nearby.: This holiday home rental outside of Wolfeboro is located on a lake, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Wolfeboro?

Choose from 53 Expedia holiday rentals in Wolfeboro for a memorable holiday.

What can I see and do in Wolfeboro?

Libby Museum and Hampshire Pewter Co. are a couple of the family-friendly sights, whereas cultural attractions include Wright Museum and New Hampshire Boat Museum. Other places in town to visit include Clark House Museum and Wolfeboro Abenaki Ski Area.

What are holiday rentals like in Wolfeboro?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wolfeboro. Holiday rentals offer amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family gatherings.