Photo by Heather Larson

Wolfeboro Holiday Rentals

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Holiday Rentals in Wolfeboro

Fridge, microwave, oven, stovetop
Lakefront home on Ossipee Lake with dock and gorgeous views
10.0 out of 10, Exceptional, (11)
"The property was great and the owner was very responsive. It was everything we needed and looking forward to staying again in the future!"
Lakefront home on Ossipee Lake with dock and gorgeous views
Fridge, microwave, oven, stovetop
Dog-friendly home with a pool table, washer/dryer, firepit & beach access
9.0 out of 10, Wonderful, (4)
"We stayed her with our five kids and a dog. The place had a great game room set away from the living room for our three teenage boys to hang out in and be boys. The girls had the living room so plenty of space when they needed a break from each other. It was pretty expensive tho. Figured it would be nice to have toilet paper, some dishwasher tabs, paper towels...basic stuff that most vrbo homes to start out with. All in all it good stay."
Dog-friendly home with a pool table, washer/dryer, firepit & beach access
Exterior
Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach
9.4 out of 10, Exceptional, (70)
"We stayed in excellent VRBO rentals before. Only problem was garbage from previous rentals had never been removed from property. As snow melted we found an old cigar but on deck as well as dog poop. Which we picked up ourselves. The were many different conflicting instructions on what not to do and what to do in regards to heat, water, dishwasher (there is no dishwasher), but there were pods for one? Otherwise, we had fun. Would recommend streamlining instructions, and removing trash as we had...
Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach
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TV, fireplace, DVD player
Waterfront home with wraparound deck, floating fireplace, deck, & firepit
7.0 out of 10, Good, (12)
"Other than the lack if dusting and sweeping the stay was wonderful and peacful."
Waterfront home with wraparound deck, floating fireplace, deck, & firepit
Private kitchen
Newly Renovated Rustic Cabin
9.8 out of 10, Exceptional, (243)
"Nicely finished home with comfortable amenities. Suggest a deep clean and updated kitchenware. Comfortable beds."
Newly Renovated Rustic Cabin
Property grounds
Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock
9.6 out of 10, Exceptional, (118)
"If you are seeing a concert at Bank of NH pavilion, look no further. Venue is a quick walk (no more then 10 minutes) on a tiny, lit path behind the motel. Steps away from a gorgeous beach with chairs provided. We were so happy we came a day early to enjoy it. Lake view from the balcony. Place was not fancy by any means but very clean and had everything you may need. We will be back!"
Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock
Interior
Vrbo Property
7.4 out of 10, Good, (3)
"Great lake access. The house was in a good location. The house needs a little TLC."
Vrbo Property
Outdoor dining
Fully renovated, dog-friendly home with private beach access & golf nearby
8.8 out of 10, Excellent, (3)
"Outdoor deck was not safe especially the steps leading to deck. The house was clean and exactly as it appeared on site. Not enough towels or toilet paper for 7 people. We had to run out and purchase toilet paper, only 2 already opened rolls were at property. Overall a beautiful place and neighborhood. Would definitely stay again."
Fully renovated, dog-friendly home with private beach access & golf nearby
Property grounds
Beautiful cottage in the Lakes Region on Hermit Lake
10.0 out of 10, Exceptional, (6)
"Gray stay! Central to 93 N to get up the the White Mountains and about 30 minutes from the major lake towns. Beautiful property!"
Beautiful cottage in the Lakes Region on Hermit Lake
Interior
Pet-friendly Waterfront Cottage: On-site Bunkhouse
3.5 star property
Pet-friendly Waterfront Cottage: On-site Bunkhouse
Indoor pool
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
10.0 out of 10, Exceptional, (147)
"Hi Malini, Thank you so much for a wonderful stay! It was exactly what we wanted/needed for the weekend. Cheers, Gabe"
The price is NZ$3,919
per night
3 Jun - 4 Jun
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
TV, fireplace, DVD player, books
Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit
9.0 out of 10, Wonderful, (51)
"Great!"
Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit
Interior
Grand Blanc Mountain Home
9.8 out of 10, Exceptional, (81)
"Overall, what an amazing place, Well kept and very clean. Internet was kind of unreliable, didn't reach a lot of places but we made due. Biggest complaint, I reached out by text to 2 different numbers but never got a response. They weren't big issues, but still. I've been renting thru VRBO for many years and this is by far my family's favorite."
Grand Blanc Mountain Home
Beach nearby, sun-loungers, beach towels
Cozy Lake Retreat: Shell Camp Lake Couples get way. Centrally located
10.0 out of 10, Exceptional, (27)
"Lisa is a spectacular host and her property was gorgeous! My boyfriend, pup and I had a quiet, relaxing getaway from our busy lives. We walked the neighborhood and enjoyed the views of the pond. I wish we had stayed longer, but we would definitely come back! Thank you again!! 😊"
The price is NZ$459
per night
30 May - 31 May
Cozy Lake Retreat: Shell Camp Lake Couples get way. Centrally located
Property grounds
Gorgeous Waterfront Condo with Lake Access & Views
10.0 out of 10, Exceptional, (15)
"We loved our stay at this cozy home. My husband and I stayed there for six nights. they were very accommodating to our needs . the house had everything we needed. It s two bedrooms, two baths was the perfect size for us . We were able to have meals and cook or go out to each. in a wonderful fireplace. Beautiful views. Everything we needed was close . We would definitely stay here again. Thank you to Rahna and staff. Awesome!"
The price is NZ$513
per night
29 May - 30 May
Gorgeous Waterfront Condo with Lake Access & Views
Interior
Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome
10.0 out of 10, Exceptional, (137)
"The Meredith Cottage is an oasis away from home. The owners have considered all the details and amenities one needs while staying there. The house is very well stocked, beautifully decorated and comfortable. Location is walking distance to great shops and restaurants. Highly recommend!"
The price is NZ$1,208
per night
27 Jun - 28 Jun
Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome
Terrace/patio
Lakefront studio with private dock, fast WiFi & full kitchen - dog-friendly
10.0 out of 10, Exceptional, (23)
"We had an amazing stay. The cottage was nice and the view from the front deck was beautiful. My only criticism is They state towels provided however my husband and I were there for 10 days and there were only 4 bath towels. That is def not enough towels. If there was a washer dryer that would be fine but there is not. So we had to go and buy more towels. Other than that it was wonderful"
Lakefront studio with private dock, fast WiFi & full kitchen - dog-friendly
TV, fireplace, DVD player, table football
Lakeside home with water views, firepit, deck, fireplace, & W/D - dog-friendly
7.0 out of 10, Good, (2)
"Horrible infestation in the basement. A caterpillar was underneath my blanket & it’s hairs got stuck in my skin. Which caused burning, itching, hives $ prickling. My one year old also got some of the hair on him & broke out in hives. When I called customer service, the property manager never got back to me. There was no apology, no nothing. This property shouldn’t be rented out if there’s an infestation. Especially when young children are staying there. It’s been 2 days since the incident & my...
Lakeside home with water views, firepit, deck, fireplace, & W/D - dog-friendly
Beach nearby
Lakefront condo with WiFi, private beach, full kitchen, & outdoor pool
7.8 out of 10, Good, (31)
"The s elk of cigarette smoke was off the charts, but then there weee the little thing d. Likescreen doo falling right off the rails. Klthu m"
Lakefront condo with WiFi, private beach, full kitchen, & outdoor pool
Interior
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet
9.0 out of 10, Wonderful, (16)
"Great time."
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet
Don't see what you're looking for?
See all available properties in Wolfeboro
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.

Other types of properties in Wolfeboro you may be interested in

Lobby
Lake Wentworth Inn
2.0 star property
9.4 out of 10, Exceptional, (338)
"Great location! Convenient to market and restaurants. Beach access directly behind Inn was a dream come true for me. "
The price is NZ$351
per night
2 Jun - 3 Jun
Lake Wentworth Inn
Exterior
The Windrifter Resort
2.5 star property
8.8 out of 10, Excellent, (151)
"Nice place, room was spacious and very clean. Staff was great, very friendly and accommodating. Issue was that the main bed was a Murphy bed, and not very supportive or comfortable. (Room was big enough where bed did not have to be a Murphy bed). Don’t know if my back could have handled it for another day or 2. Did not say that in room description. Stated it was a queen bed and sleeper sofa. "
The price is NZ$172
per night
2 Jun - 3 Jun
The Windrifter Resort
Exterior
The Wolfeboro Inn
3.5 star property
8.0 out of 10, Very good, (407)
"Stay was great and Shawn and the rest of the staff were extremely helpful and accommodating. We'll definitely look to stay here on our future trips to the area."
The price is NZ$346
per night
11 Jun - 12 Jun
The Wolfeboro Inn
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.

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 Hampshire Pewter Co., 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?

Lakefront home on Ossipee Lake with dock and gorgeous views : This holiday home rental outside of Wolfeboro is located on the beach, and has a BBQ, a selection of books and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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?

Hampshire Pewter Co. and New Hampshire Boat Museum are a couple of the family-friendly sights, whereas cultural attractions include Wolfeboro Institute of the Arts and Wright Museum. Other places in town to visit include Lake Winnipesaukee and Lake Wentworth.

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.

Recent reviews of Wolfeboro properties
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