Photo by Claudia Sanchez de Lozada

Guilford Holiday Rentals

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Our top choices for Guilford holiday rentals

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 NZ$764
includes taxes & fees
19 Jan - 20 Jan 2026
Stunning Glass House nestled in the Vermont wilderness!
The price is NZ$722
includes taxes & fees
10 Jan - 11 Jan 2026
Vikings Villages Resort - Double Bed Room
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is NZ$441
includes taxes & fees
15 Jan - 16 Jan 2026
Wellness Getaway with a Personal Sauna, and Private River Beach!
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 NZ$526
includes taxes & fees
11 Jan - 12 Jan 2026
Lake Whitingham & Mount Snow Area Village Apartment

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 NZ$479
includes taxes & fees
4 Jan - 5 Jan 2026
Downtown Hot Tub Escape

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 NZ$346
includes taxes & fees
5 Jan - 6 Jan 2026
Lovely 2nd Floor Apartment
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 NZ$814
includes taxes & fees
13 Jan - 14 Jan 2026
Terrific 3-bedroom unit in charming Leverett with AC
The price is NZ$343
includes taxes & fees
6 Jan - 7 Jan 2026
Rose wisteria 4 guests 2 bedrooms-full+queen beds
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is NZ$759
includes taxes & fees
13 Jan - 14 Jan 2026
Mountain Chalet mins from Mt Snow Skiing/hiking
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is NZ$432
includes taxes & fees
4 Jan - 5 Jan 2026
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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 NZ$562
includes taxes & fees
27 Jan - 28 Jan 2026
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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 NZ$1,033
includes taxes & fees
1 Jan - 2 Jan 2026
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
9.4 out of 10, Exceptional, (58)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is NZ$540
includes taxes & fees
7 Jan - 8 Jan 2026
Family Friendly Hilltop House In Putney Vermont
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 NZ$909
includes taxes & fees
12 Jan - 13 Jan 2026
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
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 NZ$935
includes taxes & fees
4 Jan - 5 Jan 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
10.0 out of 10, Exceptional, (1)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is NZ$727
includes taxes & fees
3 Jan - 4 Jan 2026
Riverbend Berkshire East Basecamp - 3 bedrooms available
2.0 star property
The Studio with a View. Bring your dog, too!
10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is NZ$825
includes taxes & fees
20 Jan - 21 Jan 2026
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

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 NZ$628
includes taxes & fees
4 Jan - 5 Jan 2026
Florida Mountain Log Cabin
2.0 star property
The price is NZ$1,289
includes taxes & fees
29 Jan - 30 Jan 2026
Secluded Vermont Chalet w/ Sweeping Mountain Views
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

Find out more about Guilford

Everything you need to know about Guilford holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Guilford holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Guilford holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Guilford holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Guilford holiday rentals we have selected for you start as low as NZ$346 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Guilford rentals

At Expedia, we put the best Guilford holiday 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 holiday.

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. 

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.