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Guilford Vacation Rentals

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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
$335 nightly
The price is $340
Oct 12 - Oct 13
Total with taxes and fees
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
$145 nightly
The price is $157
Oct 5 - Oct 6
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A bedroom with a skylight, a bed with floral bedding, a bedside table, and a nightstand.

3. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
$92 nightly
The price is $104
Oct 30 - Oct 31
Total with taxes and fees
Cozy Vermont Tiny Home Get Away
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

4. 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.
$254 nightly
The price is $284
Nov 3 - Nov 4
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

5. 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.
$208 nightly
The price is $232
Oct 22 - Oct 23
Total with taxes and fees
Lovely 2nd Floor Apartment
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

6. 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.
$135 nightly
The price is $146
Oct 5 - Oct 6
Total with taxes and fees
Yurt Oasis in the woods of Hinsdale, NH
A wooden interior with a kitchen, bar area, and dining space.

7. 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.
$233 nightly
The price is $261
Oct 5 - Oct 6
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A garden with a wooden pergola, purple flowers, and a river view.

8. 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.
$235 nightly
The price is $263
Oct 20 - Oct 21
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

9. 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
$366 nightly
The price is $403
Oct 5 - Oct 6
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A blue house with a porch, a wooden bench, and a door.

10. 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.
$216 nightly
The price is $241
Oct 5 - Oct 6
Total with taxes and fees
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.

11. 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.
$375 nightly
The price is $424
Oct 5 - Oct 6
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A house with a staircase leading to a porch, surrounded by snow and string lights.

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

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
10.0 out of 10, Exceptional, (12 reviews)
"Nice place"
United States
Tom
$256 nightly
The price is $286
Oct 8 - Oct 9
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A wooden house with a porch lit by string lights, surrounded by snow.

13. 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.
$391 nightly
The price is $442
Oct 6 - Oct 7
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

14. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
$165 nightly
The price is $184
Nov 1 - Nov 2
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
An aerial view of a house surrounded by a forest with autumn foliage.

15. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
$505 nightly
The price is $566
Oct 28 - Oct 29
Total with taxes and fees
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

16. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
$174 nightly
The price is $197
Oct 12 - Oct 13
Total with taxes and fees
The Eagles Wing at The CHM - Private Apartment
A lakeside park with picnic tables and a concrete walkway.

17. 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
Oct 4 - Oct 5
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

18. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
$672 nightly
The price is $704
Oct 28 - Oct 29
Total with taxes and fees
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
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.
$722 nightly
The price is $807
Oct 15 - Oct 16
Total with taxes and fees
Spacious 5BR w/ Hot Tub & Games
A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

20. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.4 out of 10, Very good, (5 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
$576 nightly
The price is $645
Oct 5 - Oct 6
Total with taxes and fees
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"We stay here 2 or 3 times a year and know it well. The staff are always welcoming and helpful. On this visit, we found our original room to be noisy because of the ice machine (?), but the staff got us another room when asked. The room was spacious, quiet and comfortable. The hotel was unusually full, but very quiet. Breakfast is always good here and the coffee is excellent. (Vermont seems to be obsessed with coffee....) Having tried two or three other hotels in Brattleboro, we have settled on the Hampton Inn as our "go to" spot."
Thomas 1-night trip
Posted 13 hours ago
Hampton Inn Brattleboro

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 $261 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 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 Fort Dummer State Park and Sweet Pond 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.