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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Our top choices for Wolfeboro holiday rentals

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 NZ$333
includes taxes & fees
5 Oct - 6 Oct
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard

2. 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 NZ$642
includes taxes & fees
4 Oct - 5 Oct
9 Lake Street

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 NZ$312
includes taxes & fees
6 Oct - 7 Oct
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard

4. 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 NZ$296
includes taxes & fees
5 Oct - 6 Oct
Caretakers -Split level Pet Friendly $50 Fee

5. 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 NZ$731
includes taxes & fees
12 Oct - 13 Oct
Cozy 1BR Getaway Steps from Lake Winnipesaukee

6. 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 NZ$508
includes taxes & fees
1 Nov - 2 Nov
Downtown Wolfeboro condo, right on Wolfeboro Bay/Winnipesaukee w/dock available

7. 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 NZ$347
includes taxes & fees
25 Oct - 26 Oct
Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath

8. 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 NZ$479
includes taxes & fees
8 Oct - 9 Oct
Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath

9. 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 NZ$312
includes taxes & fees
2 Nov - 3 Nov
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath

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 NZ$454
includes taxes & fees
5 Oct - 6 Oct
Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath

11. 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 NZ$305
includes taxes & fees
25 Oct - 26 Oct
Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath

12. 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 NZ$823
includes taxes & fees
6 Oct - 7 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!

13. 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 NZ$833
includes taxes & fees
4 Oct - 5 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!

14. Newly Renovated Cottage 7 in Alton Bay

Newly Renovated Cottage 7 in Alton Bay
Alton
10.0 out of 10, Exceptional, (2 reviews)
"Host was responsive and the property was just close enough to enjoy laconia without a huge price premium. Its a simple cabin, but it did what we needed it to do. Gravel parking lot is not the best for motorcycles if i had to leave constructive feedback. Would rent again."
United States
fred j.
The price is NZ$669
includes taxes & fees
28 Oct - 29 Oct
Newly Renovated Cottage 7 in Alton Bay

15. 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 NZ$738
includes taxes & fees
8 Oct - 9 Oct
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...

16. Picturesque Studio Lakefront - Dock

Picturesque Studio Lakefront - Dock
Alton
The price is NZ$662
includes taxes & fees
12 Oct - 13 Oct
Picturesque Studio Lakefront - Dock

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 NZ$437
includes taxes & fees
3 Nov - 4 Nov
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

18. 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 NZ$640
includes taxes & fees
27 Oct - 28 Oct
Newly Renovated Cottage 4 in Alton Bay, NH

19. Cozy, Pet-Friendly Escape Near Lake & Mountains

Cozy, Pet-Friendly Escape Near Lake & Mountains
Gilford
10.0 out of 10, Exceptional, (49 reviews)
"Cute and comfortable. The host communicated well and had all the essentials available. We enjoyed our stay."
United States
Julie W.
The price is NZ$850
includes taxes & fees
4 Oct - 5 Oct
Cozy, Pet-Friendly Escape Near Lake & Mountains

20. Lake Getaway: Walk Across Street to Private Beach!

Lake Getaway: Walk Across Street to Private Beach!
Gilford
9.4 out of 10, Exceptional, (28 reviews)
"the property was a great location for my stay Host was good at returning calls/text replying to questions and concerns will rent again.. thanks"
United States
Laura C.
Lake Getaway: Walk Across Street to Private 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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Top Wolfeboro Hotel Reviews

Find out more about Wolfeboro

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wolfeboro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wolfeboro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wolfeboro. Seeing all the best attractions is bound to make you fall in love with Wolfeboro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wolfeboro short-term rentals, that won’t be hard to do.

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.