Guilford Vacation Rentals

Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Guilford vacation rentals

Living area

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
10.0 out of 10, Exceptional, (1 review)
"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.
$371 nightly
The price is $416
Jun 3 - Jun 4
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$241 nightly
The price is $244
Jun 1 - Jun 2
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
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
9.8 out of 10, Exceptional, (14 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.
$145 nightly
The price is $157
Jun 1 - Jun 2
Total with taxes and fees
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
$75 nightly
The price is $81
Jun 1 - Jun 2
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"Beautifully appointed and comfortable. "
United States
Emily Kate G.
$180 nightly
The price is $201
Jun 8 - Jun 9
Total with taxes and fees
Lovely 2nd Floor Apartment
Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (2 reviews)
"It was an excellent place to stay. Super comfy and quiet, falling asleep to the sound of the creek. Well equipped with everything you need. Good fast wifi. Excellent value for the money. Great place if you want to really get away from it all."
United States
Seva L.
$212 nightly
The price is $237
Jun 7 - Jun 8
Total with taxes and fees
Brookside cottage near the mountains and outdoor recreation
Fridge, microwave, stovetop, coffee/tea maker

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (17 reviews)
"We had a great stay! Cabin is cozy and met all of our needs for the weekend. We loved exploring the nearby trails and shops. Our dogs loved it as well :) "
United States
Kelsey M.
$383 nightly
The price is $426
Jun 15 - Jun 16
Total with taxes and fees
Hiking Trails On-Site: Cozy Falls Brook Cabin
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
$278 nightly
The price is $314
Jun 1 - Jun 2
Total with taxes and fees
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

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.6 out of 10, Exceptional, (8 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
$254 nightly
The price is $284
Jun 29 - Jun 30
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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.
$181 nightly
The price is $205
Jun 30 - Jul 1
Total with taxes and fees
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
$247 nightly
The price is $277
Jun 3 - Jun 4
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (11 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$377 nightly
The price is $426
Jun 7 - Jun 8
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
Exterior

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
$173 nightly
The price is $193
Jun 1 - Jun 2
Total with taxes and fees
Rose room Victorian home queen bed private bath
Smart TV, fireplace, Netflix, streaming services

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
$382 nightly
The price is $432
Jun 1 - Jun 2
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Outdoor dining

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Townshend
$280 nightly
The price is $314
Jun 2 - Jun 3
Total with taxes and fees
Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
$189 nightly
The price is $211
Jun 1 - Jun 2
Total with taxes and fees
Private bed with En-suite bathroom Marigold Room
House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
$376 nightly
The price is $410
Jun 15 - Jun 16
Total with taxes and fees
Hiking Trails On-site: Cozy Falls Brook Cabin
Exterior

Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.6 out of 10, Exceptional, (5 reviews)
"Nice place"
United States
Tom
$245 nightly
The price is $274
Jun 24 - Jun 25
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Beach

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (51 reviews)
"Cozy place, very close to the moover and Mount Snow. Host was very responsive. Would definitely book again!"
United States
dory p.
$249 nightly
The price is $281
Jun 7 - Jun 8
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Interior

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (8 reviews)
"Loved this place so much! Adorable spot, quaint but has everything you need. Loved the luxury details. "
United States
Carly L.
$423 nightly
The price is $478
Jun 1 - Jun 2
Total with taxes and fees
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Very clean spacious room. Quiet. Staff friendly and helpful. Breakfast buffet was ample and good choices."
Christie 1-night trip
Posted 3 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Guilford

Everything you need to know about Guilford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Guilford vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Guilford vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Guilford vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Guilford. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Guilford in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $157 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Guilford rentals

At Expedia, we put the best Guilford vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Guilford rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Guilford vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Guilford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Guilford?

Yes, there are vacation rentals close to the most popular points of interest in Guilford, or you can select a more remote option if you want a relaxing place to stay. Guilford is known for its shopping.

What are some of the best vacation rentals in Guilford?

The Jelly Mill-A Peaceful River Retreat: This highly rated vacation home rental in Guilford is located on a river and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Guilford?

Expedia has 5 vacation 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 Norcross Wildlife Sanctuary and Fort Dummer State Park.

What’s a vacation rental in Guilford like?

Vacation rentals are private properties you can reserve for a couple days or more in Guilford. Vacation rentals feature extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family trip.