Photo by mike dobias

Walpole Holiday Rentals

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Holiday Rentals in Walpole

Dog-friendly chalet cabin with valley view, deck, and private hot tub

7.6 out of 10, Good, (19)
"Absolutely loved my stay at this tiny getaway house! The space was cozy, well-designed, and had everything I needed for a relaxing escape. The peaceful surroundings and thoughtful touches made it truly special. Perfect for unplugging and recharging. Can’t wait to come back for another retreat!" "
Dog-friendly chalet cabin with valley view, deck, and private hot tub

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (151)
"Never could get the wifi to work. I entered the code on the router 6 times but no luck. Would be helpful if you changed the password for the wifi to an easily entered name. The man who came to shovel unfortunately after we were stuck in the snow was very helpful and very nice.. He got us out."
The price is AU$598
includes taxes & fees
27 Jan - 28 Jan 2025
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.

10.0 out of 10, Exceptional, (39)
"This property was beautiful, clean, well maintained, had everything we needed. Wish we could have stayed longer! Thank you for a weekend we’ll never forget! We hope to rent this house again in the future. "
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.

Riverfront studio with river view, full kitchen, & free WiFi

7.2 out of 10, Good, (10)
"Sufficient space and easy distance to center of Ludlow and Okemo Mt"
The price is AU$457
includes taxes & fees
1 Jan - 2 Jan 2025
Riverfront studio with river view, full kitchen, & free WiFi

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

9.0 out of 10, Wonderful, (22)
"This is a great cabin with stunning views!"
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!

10.0 out of 10, Exceptional, (40)
"This property was great way to spend the weekend with friends. The kitchen was well equipped, and the living room was very spacious, and the bedrooms were comfortable especially the master bedroom. I would recommend this property for anyone and would be happy to stay again when we are in the area."
Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!

17-Acre Vermont Escape w/ Panoramic Mountain Views

10.0 out of 10, Exceptional, (10)
"Great stay would highly recommend"
17-Acre Vermont Escape w/ Panoramic Mountain Views

Green Mountain Modern House: iconic modern getaway

Green Mountain Modern House: iconic modern getaway

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

10.0 out of 10, Exceptional, (75)
"This is our third trip to this property and it never disappoints! Wonderful weekend away in VT."
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views

Pristine Waterfront, Charming Home, Breathtaking Views

9.8 out of 10, Exceptional, (56)
"Beautiful leaves in reds, oranges, and yellows reflected in a gorgeous pond with a pair of loons slowly floating by....Perfection! What a gorgeous location! We had a great stay- the kitchen was wonderful to cook in- we loved the gas stove- bacon tasted so delicious with croissants in the morning! The house is large and comfortable- cozy couch, large piano, washer and dryer, tv, and wifi. We have to agree with other guests- the bed is squeaky....ridiculously squeaky.....to the point of...
Pristine Waterfront, Charming Home, Breathtaking Views

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (53)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is AU$555
includes taxes & fees
5 Jan - 6 Jan 2025
Family Friendly Hilltop House In Putney Vermont

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

6.6 out of 10, (12)
"My boyfriend and I (and our dog) really enjoyed this place. It’s on a quiet road, tucked up into a woodsy hill which gives the feeling of being secluded, while in actuality not being far from a main road. The listing is pretty accurate; the house is absolutely covered in windows, which allows for plenty of fresh air and natural light. The master bed is super comfortable, and the master bathroom is really nice too. I was a little apprehensive about the lack of air conditioning, but there is a...
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Cozy Falls Brook Cabin: Hike & Swim On-Site!

10.0 out of 10, Exceptional, (10)
"The cabin is immaculate and very cute and cozy. It's lovely to be right by the brook in a quiet neighborhood set in a woodsy area. Lots of great places a short right away too. Brattleboro is lots of fun, and we loved hiking in the Manitou Project."
Cozy Falls Brook Cabin: Hike & Swim On-Site!

Two-story, dog-friendly house with wood fireplace

8.6 out of 10, Excellent, (28)
"House was awesome! Fit a large group well! Would recommend for sure!"
Two-story, dog-friendly house with wood fireplace

Two-story townhome with forest/mountain view, gas fireplace, pool, gym & saunas

8.6 out of 10, Excellent, (10)
"The place is great but it alludes that the pool and gym are included, they are in fact not and they want you to pay another $25 per person to use them. So I wasn't really happy about that."
Two-story townhome with forest/mountain view, gas fireplace, pool, gym & saunas

Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

9.6 out of 10, Exceptional, (40)
"The owner had the place ready to go when we arrived. It was a late arrival, but there were outside lights that were warm and inviting. Plenty of space for our party of 12 (6 adults and 6 kids). Kitchen was welled stocked with cooking necessities, great hangout spaces in the basement and first floor, and a convenient space for ski boots and outer gear in the basement near parking. Kids absolutely loved the pool - and have the pruned hands to prove it. The location couldn't have been better, ~25...
Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

Cozy Camp in the woods surrounded by nature.!

10.0 out of 10, Exceptional, (11)
"Beautiful setting, quiet, bucolic. Cabin super clean and rustic. Well equipped, clean gym. Owners are super and very kind. A "
Cozy Camp in the woods surrounded by nature.!

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

10.0 out of 10, Exceptional, (50)
"Peaceful, beautiful property. Was a relaxing stay, had everything we needed. "
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

9.8 out of 10, Exceptional, (15)
"Very nice house and property! "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
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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Other types of properties in Walpole you may be interested in

Pointe at Castle Hill Resort

3.5 star property
8.8 out of 10, Excellent, (770)
"It was a very nice place and the staff was very friendly."
The price is AU$310
includes taxes & fees
20 Jan - 21 Jan 2025
Pointe at Castle Hill Resort

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1001)
"Like size of room"
The price is AU$156
includes taxes & fees
9 Jan - 10 Jan 2025
Colonial Motel And Spa

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (1000)
"Room with 2 queens was very spacious. "
The price is AU$164
includes taxes & fees
12 Jan - 13 Jan 2025
Hampton Inn Brattleboro
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.

Frequently asked questions

Can I find a holiday rental in Walpole?

Yes, there are holiday rentals in Walpole close to Pete's Stand Vegetables, or you can select a more secluded option if you're looking for a relaxing stay. Walpole is known for its shopping and golf courses. Make sure you have time to check out the restaurants and art during your trip.

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

Dog-friendly chalet cabin with valley view, deck, and private hot tub: This holiday home rental outside of Walpole offers a patio, a selection of games and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals will I find in Walpole?

Choose from 4 Expedia holiday rentals in Walpole for a memorable holiday.

What’s there to see and do in Walpole?

Family-friendly attractions include Pete's Stand Vegetables, whereas Connecticut River is a spot to enjoy the outdoors. Walpole Mountain View Winery and Walpole Artisans Cooperative are other places to visit while you're in town.

What’s a holiday rental in Walpole like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Walpole. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip or a small group gathering.