A red covered bridge with a sign indicating a legal load limit of 16,000 pounds.

Guilford Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Guilford vacation rentals

A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

1. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is CA $389
CA $481 total
includes taxes & fees
Sep 29 - Sep 30
Vikings Villages Resort - Double Bed Room
A rustic cabin with a covered porch, a small shed, and outdoor seating.

2. 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, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is CA $127
CA $223 total
includes taxes & fees
Oct 5 - Oct 6
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

3. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.4 out of 10, Exceptional, (10 reviews)
"What an amazing Yurt. The location was so peaceful. The yurt and outhouse was super clean. Hosts were friendly and helpful. I would stay again if in the area."
United States
Troy H.
The price is CA $116
CA $202 total
includes taxes & fees
Sep 29 - Sep 30
Yurt Oasis in the woods of Hinsdale, NH
A room with white paneled walls, a wooden bench, a teal cushion, a vase with flowers, a framed picture, and a shelf with books and a small electronic device.

4. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is CA $112
CA $159 total
includes taxes & fees
Oct 29 - Oct 30
Cozy Vermont Tiny Home Get Away
A wooden interior with a kitchen, bar area, and dining space.

5. 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, (5 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.
The price is CA $176
CA $368 total
includes taxes & fees
Sep 30 - Oct 1
The Studio with a View. Bring your dog, too!
A lakeside park with picnic tables and a concrete walkway.

6. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is CA $78
CA $115 total
includes taxes & fees
Sep 29 - Sep 30
2 private mountain RV pads for rent. Full hook ups
A wooden house with a porch lit by string lights, surrounded by snow.

7. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (16 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is CA $99
CA $537 total
includes taxes & fees
Sep 29 - Sep 30
Chalet Mount Snow/Stratton Skiing/hiking
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

8. 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 CA $240
CA $418 total
includes taxes & fees
Oct 20 - Oct 21
Wellness Getaway with a Personal Sauna, and Private River Beach!
A blue house with a porch, a wooden bench, and a door.

9. 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, (9 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is CA $127
CA $341 total
includes taxes & fees
Oct 5 - Oct 6
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

10. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (48 reviews)
"Once we got to know the fireplace, it was a wonderful addition to a very cozy cabin. The house felt loved and each different room had different touches of character and magic. We absolutely loved our stay. "
United States
Sarah K.
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

11. 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.
The price is CA $71
CA $428 total
includes taxes & fees
Sep 29 - Sep 30
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

12. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is CA $206
CA $570 total
includes taxes & fees
Oct 5 - Oct 6
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

13. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is CA $197
CA $329 total
includes taxes & fees
Oct 22 - Oct 23
Lovely 2nd Floor Apartment
A two-story white house with a red door, surrounded by autumn foliage and a stone wall.

14. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (4 reviews)
"Open modern clean space in a lovely quiet location. The hosts were very responsive and helpful. We would be happy to visit again."
United States
Matthew C.
The price is CA $147
CA $198 total
includes taxes & fees
Sep 30 - Oct 1
The Eagles Wing at The CHM - Private Apartment
A garden with a wooden pergola, purple flowers, and a river view.

15. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is CA $188
CA $371 total
includes taxes & fees
Oct 20 - Oct 21
Family Friendly Hilltop House In Putney Vermont
A calm lake with a wooden boat on the shore.

16. 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, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is CA $144
CA $441 total
includes taxes & fees
Oct 13 - Oct 14
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

17. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is CA $153
CA $281 total
includes taxes & fees
Oct 20 - Oct 21
Rose room Victorian home queen bed private bath
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

18. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is CA $170
CA $303 total
includes taxes & fees
Oct 18 - Oct 19
Private bed with En-suite bathroom Marigold Room
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

19. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is CA $406
CA $924 total
includes taxes & fees
Sep 29 - Sep 30
Spacious 5BR w/ Hot Tub & Games
A hallway with wooden flooring, white walls, and a bed in the background.

20. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is CA $297
CA $605 total
includes taxes & fees
Sep 29 - Sep 30
Cozy private 2 bed apartment in Shelburne Falls
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Guilford Hotel Reviews

Latchis Hotel

Latchis Hotel

10/10 Excellent
"This place is a gem. I love and like the proximity to the train station, Brattleboro Food Coop, River Art School and Brattleboro Museum and Art Center, I visited twice: first with my teen son and husband, and the second by myself, and both times were great. There are signs of the passing of time in this lovely Art Deco structure, and that adds to its beauty, Super courteous staff The first time we watched a movie, so if you stay at the hotel, please treat yourself to that or some of their baskets. I missed eating at their restaurant, so I guess next time. My husband loved that there was always coffee for him, and my son loved our mini fridge and microwave. We love the history of this place and how is part of the larger arts and culture scene of Brattleboro"
Juana 2-night trip
Posted 2 hours ago
Latchis Hotel

Find out more about Guilford

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Guilford. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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 7 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 Sweet Pond State Park 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.