Walpole Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Walpole holiday rentals

TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is HK$1,752
HK$2,088 total
includes taxes & fees
13 May - 14 May
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Terrace/patio

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (12 reviews)
"Stacy and her husband were very communicative and accommodating. We had everything we needed in the yurt and they provided us with some extra supplies as well. Would definitely stay again!"
United States
Gina M.
The price is HK$705
HK$1,232 total
includes taxes & fees
13 May - 14 May
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Outdoor dining

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is HK$431
HK$637 total
includes taxes & fees
13 May - 14 May
2 private mountain RV pads for rent. Full hook ups
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"3rd year at this listing, absolutely love it. Close to okemo and mount snow. Host got back to me very quickly when reached out to. "
United States
Jake D.
The price is HK$1,331
HK$2,823 total
includes taxes & fees
14 May - 15 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.8 out of 10, Exceptional, (22 reviews)
"Amazing weekend stay with our pup! Looking forward to staying here in the summer! "
United States
Naydene G.
The price is HK$1,409
HK$2,913 total
includes taxes & fees
13 May - 14 May
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Exterior

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is HK$1,253
HK$2,245 total
includes taxes & fees
28 May - 29 May
Wellness Getaway with a Personal Sauna, and Private River Beach!
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,374
HK$2,512 total
includes taxes & fees
26 May - 27 May
Family Friendly Hilltop House In Putney Vermont
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$550
HK$2,973 total
includes taxes & fees
13 May - 14 May
Chalet Mount Snow/Stratton Skiing/hiking
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (21 reviews)
"Great time easy to get to clean quiet and peaceful definitely would recommend for romantic getaway "
United States
Garrett B.
The price is HK$2,153
HK$2,676 total
includes taxes & fees
26 May - 27 May
Owl's Nest Treehouse
Interior

Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
The price is HK$1,174
HK$1,878 total
includes taxes & fees
13 May - 14 May
Cozy Tiny House on Main Street. Fully Renovated.
TV

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
The price is HK$1,331
HK$2,404 total
includes taxes & fees
17 May - 18 May
Brook Road Cabin
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (23 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is HK$1,397
HK$2,697 total
includes taxes & fees
20 May - 21 May
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Smart TV, fireplace

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Londonderry
10.0 out of 10, Exceptional, (10 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
The price is HK$1,938
HK$5,029 total
includes taxes & fees
20 May - 21 May
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Smart TV, fireplace, stereo

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is HK$2,372
HK$3,761 total
includes taxes & fees
13 May - 14 May
LUXE Forest Retreat
Sauna

Magic Mountain Trailside Condo - Ski In / Ski Out

Magic Mountain Trailside Condo - Ski In / Ski Out
Londonderry
9.8 out of 10, Exceptional, (14 reviews)
"Nice and we enjoyed our stay"
United States
Gretchen H.
The price is HK$979
HK$2,450 total
includes taxes & fees
11 Jun - 12 Jun
Magic Mountain Trailside Condo - Ski In / Ski Out
Terrace/patio

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (19 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is HK$1,057
HK$2,981 total
includes taxes & fees
1 Jun - 2 Jun
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Property grounds

Lake Front Family Friendly Escape

Lake Front Family Friendly Escape
Newport
10.0 out of 10, Exceptional, (4 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is HK$1,057
HK$2,973 total
includes taxes & fees
14 May - 15 May
Lake Front Family Friendly Escape
Interior

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is HK$1,761
HK$4,700 total
includes taxes & fees
13 May - 14 May
Terrific 3-bedroom cottage with AC in charming Cavendish
Interior

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
The price is HK$1,714
HK$3,893 total
includes taxes & fees
5 Jun - 6 Jun
Cozy Private Cabin in Andover - Fireplace & Hot tub
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 Walpole Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very clean. Well equipped kitchen. Helpful staff."
Pamela 2-night trip
Posted 1 hour ago
Pointe at Castle Hill Resort

Find out more about Walpole

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

Frequently asked questions

Can I find a holiday rental in Walpole?

Yes, there are holiday rentals in Walpole close to Walpole Artisans Cooperative, 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?

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna: This holiday home rental outside of Walpole is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Walpole?

North Walpole Village Park and Connecticut River are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Pete's Stand Vegetables. Walpole Town Hall 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.