Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, 26 reviews
"Very cozy little house, close to everything, great hikes, and downtown was very cute!"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
10.0 out of 10, Exceptional, 40 reviews
"We had a wonderful stay. Peace and quiet is priceless for city folks like us. The place was very clean and adequately equipped. Communication was top notch. Would stay here again!"
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Charming Waterfront Log Cabin
9.8 out of 10, Exceptional, 28 reviews
"Great getaway from the rat race!"
The price is AU$726
includes taxes & fees
26 July - 27 July
Charming Waterfront Log Cabin
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Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, 37 reviews
"The beautiful drive to this location was worth the trip! Lovely on every account! The tips for local sights and activities made us wish we were there longer!"
Cozy Cottage Along Idyllic Green River
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, 25 reviews
"We had a great stay at Labrador Lodge! The house was comfortable and cozy. The layout of the home worked perfectly for our family and we loved being together on the quiet mountain road. The beautiful, large screen porch was our favorite part!"
Beautiful, private log cabin with huge, relaxing screened porch
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, 22 reviews
"This property is fairytale cute, so welcoming and relaxing. We had a beautiful stay in Vermont thanks to this location. And there were surprise puppies on site!!!!! Honestly this was the kind of trip that gives you confidence in vacation rentals. Clean, wonderfully decorated, off the beaten path a truly relaxing stay! Go outside at night!!!! We dont have stars like that in the city."
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Downtown Hot Tub Escape
9.2 out of 10, Wonderful, 5 reviews
"The house was adorable! Great place for a getaway! We did realize almost all of the cups were dirty so we cleaned a lot our first day there. We also had issues with the hot water. As a group of 8 and only one bathroom we made it work but not having hot water was rough! Oh and blowing the fuse anytime we wanted to coffee! But for an old home it was nice!"
The price is AU$532
includes taxes & fees
23 July - 24 July
Downtown Hot Tub Escape
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, 10 reviews
"Peaceful, restful and great location."
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
9.8 out of 10, Exceptional, 8 reviews
"Beautiful property, amazing views, wonderful owners, warm sauna—what else could you want? Highly recommend!"
The price is AU$654
includes taxes & fees
5 July - 6 July
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, 41 reviews
"The property was exactly what I was expecting. Check-in was simple and the property was very clean."
Spectacular Mountain views with all the amentities nearby
Hilltop Home with Great Views
9.2 out of 10, Wonderful, 12 reviews
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
The price is AU$514
includes taxes & fees
31 July - 1 Aug
Hilltop Home with Great Views
Beautiful Mt area with beautiful scenic views; 6 miles to Mount Snow Ski Resort.
9.4 out of 10, Exceptional, 10 reviews
"We loved our stay and would definitely come back."
Beautiful Mt area with beautiful scenic views; 6 miles to Mount Snow Ski Resort.
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, 36 reviews
"The scenery and ambiance of the property won us over right away. Slept on the veranda with the windows open, listening to the wildlife and waking to the views of the lake. Was a great place, sorry it was so chilly in the mornings…can’t do much about the weather :)"
Waterfront Cottage on Scenic Sportsman Pond
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
6.0 out of 10, 8 reviews
"We loved staying in the Newfane home! I was a bit worried at 1st from reading the reviews but it was great. The house was nice and cozy. The sauna and steam tub were AMAZING. We really enjoyed the quiet and we were so close to such great restaurants. We would love to come back!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Cozy Falls Brook Cabin: Hike & Swim On-Site!
10.0 out of 10, Exceptional, 4 reviews
"What a beautiful clean cabin nestled next to a brook with lots of hiking paths to explore. Centrally located to several ski resorts. Matt was the most excellent host! I look forward to returning during other seasons!"
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, 9 reviews
"It’s a wonderful place to stay!!"
Lakefront Orange Vacation Rental - Pet Friendly!
Rustic Retreat: Cozy Log Cabin
9.6 out of 10, Exceptional, 5 reviews
"It was so peaceful and restful, we didn't even want to go anywhere else and do anything, but stay at the cabin and relax."
Rustic Retreat: Cozy Log Cabin
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, 24 reviews
"Our stay was absolutely amazing we will definitely be visiting this property again."
Jacksonville Cabin w/ Wraparound Deck & Views
Family Friendly Hilltop House In Putney Vermont
9.6 out of 10, Exceptional, 51 reviews
"This is a large property. We were able to relax and enjoy ourselves. The beds were amazing and everything was fresh and clean. Although the owner is on sight, we had complete privacy. The kitchen is well appointed with everything you need to make a wonderful Vermont meal. 10 out of 10. We’d stay again!"
Family Friendly Hilltop House In Putney Vermont
A vacation destination in Southern Vermont
10.0 out of 10, Exceptional, 60 reviews
"The cabin was adorable. The kitchen had everything we needed. Close to Mount Snow for us to ski. The yard was beautiful, and our pup loved it. We walked to the lake through the woods. The garage entrance was perfect for after skiing and to clean the dog after playing in the yard. It was also very clean."
A vacation destination in Southern Vermont
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See all available properties in Chesterfield
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.

Chesterfield Holiday Home Travel Info

Other types of properties in Chesterfield you may be interested in

Colonial Motel And Spa
3.0 star property
6.8 out of 10, 1,005 reviews
"Great spot"
The price is AU$161
includes taxes & fees
7 July - 8 July
Colonial Motel And Spa
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very good, 1,002 reviews
"Older, but well maintained. "
The price is AU$180
includes taxes & fees
7 July - 8 July
The Covered Bridge Inn
Hampton Inn Brattleboro
2.5 star property
8.4 out of 10, Very good, 918 reviews
"Very good"
The price is AU$247
includes taxes & fees
16 July - 17 July
Hampton Inn Brattleboro
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.

Everything you need to know about Chesterfield 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 Chesterfield 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 Chesterfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield 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 Chesterfield holiday rentals we have selected for you start as low as AU$514 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield 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 Chesterfield 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 Chesterfield 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 Chesterfield. 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 a holiday rental in Chesterfield?

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

What can I see and do in Chesterfield?

Explore the area and family-friendly sights such as Brattleboro Bowl, or get out into nature at a spot like Pisgah State Park. Asbury United Methodist Church and Spofford Lake are a couple of places you'll find in the wider area.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals offer amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for families.

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