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Guilford Holiday Rentals

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Check prices for these dates

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Guilford holiday rentals

Interior
Stunning Glass House nestled in the Vermont wilderness!

Holiday Home in Guilford

Stunning Glass House nestled in the Vermont wilderness!
10.0 out of 10, Exceptional, (1)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
The price is HK$1,251
HK$3,446 total
includes taxes & fees
19 Jan - 20 Jan 2026
Stunning Glass House nestled in the Vermont wilderness!
Exterior
Vikings Villages Resort - Double Bed Room

Chalet in Guilford

Vikings Villages Resort - Double Bed Room
The price is HK$2,137
HK$2,797 total
includes taxes & fees
28 Dec - 29 Dec
Vikings Villages Resort - Double Bed Room
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment

Apartment in Whitingham

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is HK$1,088
HK$2,367 total
includes taxes & fees
29 Dec - 30 Dec
Lake Whitingham & Mount Snow Area Village Apartment
Exterior
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Apartment in Dover

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
9.2 out of 10, Wonderful, (17)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is HK$428
HK$2,399 total
includes taxes & fees
27 Jan - 28 Jan 2026
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior detail
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Apartment in Greenfield

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
9.0 out of 10, Wonderful, (4)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is HK$692
HK$1,859 total
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Interior
Lovely 2nd Floor Apartment

Holiday Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (46)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
The price is HK$902
HK$1,563 total
includes taxes & fees
28 Dec - 29 Dec
Lovely 2nd Floor Apartment
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is HK$1,049
HK$1,976 total
includes taxes & fees
19 Jan - 20 Jan 2026
Wellness Getaway with a Personal Sauna, and Private River Beach!
Exterior
Terrific 3-bedroom unit in charming Leverett with AC

Apartment in Leverett

Terrific 3-bedroom unit in charming Leverett with AC
10.0 out of 10, Exceptional, (1)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
The price is HK$1,749
HK$3,611 total
includes taxes & fees
29 Dec - 30 Dec
Terrific 3-bedroom unit in charming Leverett with AC
Interior
Wilmington Retreat Near Trails, Skiing & Festivals

Cottage in Wilmington

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveller
The price is HK$1,515
HK$4,674 total
includes taxes & fees
28 Dec - 29 Dec
Wilmington Retreat Near Trails, Skiing & Festivals
TV
Florida Mountain Log Cabin

Holiday Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is HK$1,591
HK$2,841 total
includes taxes & fees
4 Jan - 5 Jan 2026
Florida Mountain Log Cabin
Exterior
2 Twin beds on 1st floor with En-suite bathroom.

Apartment in Shelburne Falls

2 Twin beds on 1st floor with En-suite bathroom.
The price is HK$598
HK$1,267 total
includes taxes & fees
28 Dec - 29 Dec
2 Twin beds on 1st floor with En-suite bathroom.
Terrace/patio
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Chalet in Dover

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is HK$655
HK$3,120 total
includes taxes & fees
5 Jan - 6 Jan 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Property grounds
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.0 out of 10, Wonderful, (45)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
The price is HK$777
HK$2,389 total
includes taxes & fees
14 Jan - 15 Jan 2026
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available

Holiday Home in Charlemont

Riverbend Berkshire East Basecamp - 3 bedrooms available
10.0 out of 10, Exceptional, (1)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is HK$1,243
HK$3,281 total
includes taxes & fees
3 Jan - 4 Jan 2026
Riverbend Berkshire East Basecamp - 3 bedrooms available
TV, books
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Cottage in Walpole

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is HK$1,855
HK$2,181 total
includes taxes & fees
28 Dec - 29 Dec
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Microwave, oven, stovetop
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

Chalet in Wardsboro

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
10.0 out of 10, Exceptional, (4)
"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."
United States
Kristen T.
The price is HK$1,632
HK$4,004 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Terrace/patio
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Chalet in Wardsboro

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is HK$1,671
HK$3,697 total
includes taxes & fees
20 Jan - 21 Jan 2026
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Holiday Home in Keene

Downtown Hot Tub Escape
9.6 out of 10, Exceptional, (21)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is HK$1,123
HK$2,323 total
includes taxes & fees
30 Dec - 31 Dec
Downtown Hot Tub Escape
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Chalet in East Dover

Mountain Chalet mins from Mt Snow Skiing/hiking
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$1,039
HK$3,510 total
includes taxes & fees
13 Jan - 14 Jan 2026
Mountain Chalet mins from Mt Snow Skiing/hiking
Outdoor dining
Charming Home Walk to Downtown!

Holiday Home in Keene

Charming Home Walk to Downtown!
10.0 out of 10, Exceptional, (2)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is HK$1,733
HK$4,815 total
includes taxes & fees
22 Jan - 23 Jan 2026
Charming Home Walk to Downtown!
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 Guilford Hotel Reviews

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

10/10 Excellent
"Checkin was quick. I like the pre-check in process."
Anthony 1-night trip
Posted 3 days ago
Days Inn by Wyndham Keene NH

Find out more about Guilford

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

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

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

Frequently asked questions

Can I find holiday rentals in Guilford?

Yes, there are holiday rentals close to the most popular sights in Guilford, or you can select a more secluded option if you're looking for a relaxing stay. Guilford is known for its shopping.

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

The Jelly Mill-A Peaceful River Retreat: This highly rated holiday home rental in Guilford is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, 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 Guilford?

Expedia has 4 holiday rentals for your stay in Guilford.

What’s there to see and do in Guilford?

Explore the area and family-friendly sights such as Brattleboro Bowl, or get out into nature at a spot like Brattleboro Common. Other places in town to visit include Sweet Pond State Park and Fort Dummer State Park.

What’s a holiday rental in Guilford like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Guilford. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.