Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Owl's Nest Treehouse

Alstead
10.0 out of 10, Exceptional, (13)
"Great place . Would highly recommend it.!"
United States
Peter G.
The price is AU$512
includes taxes & fees
14 Dec - 15 Dec
Owl's Nest Treehouse

FaLL Western Mass Getaway-Airhockey-Firepit

Colrain
9.8 out of 10, Exceptional, (38)
"Great house for family gatherings "
United Kingdom
John Paul B.
The price is AU$974
includes taxes & fees
10 Dec - 11 Dec
FaLL Western Mass Getaway-Airhockey-Firepit

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Fitzwilliam
10.0 out of 10, Exceptional, (10)
"This house is amazing. "
United States
Amanda Q.
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Lovely 2nd Floor Apartment

Greenfield
10.0 out of 10, Exceptional, (45)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
The price is AU$308
includes taxes & fees
14 Dec - 15 Dec
Lovely 2nd Floor Apartment

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington
10.0 out of 10, Exceptional, (108)
"Met family here and was a fantastic place for get together "
United States
Melissa C.
Beautiful Custom Built Timber Frame Home, Sleeps 11

The Jelly Mill-A Peaceful River Retreat

Guilford
10.0 out of 10, Exceptional, (64)
"Beautiful rural location next to the Green River. A peaceful relaxing place to stay. We would love to stay here again "
United States
Georgene M.
The Jelly Mill-A Peaceful River Retreat

LUX property, Stunning views, private setting,pet welcome, fire pit ,WIFI,AC,EV

Townshend
10.0 out of 10, Exceptional, (7)
LUX property, Stunning views, private setting,pet welcome, fire pit ,WIFI,AC,EV

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Townshend
10.0 out of 10, Exceptional, (62)
"Another great summer vacation with family at this beautiful property! Have already booked for next year."
United States
Shirlee B.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Wilmington
8.6 out of 10, Excellent, (64)
"Great location and super cute"
United States
Jeff S.
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cozy Updated Log Cabin with Mountain Views close to Monadnock

Fitzwilliam
9.4 out of 10, Exceptional, (29)
"a fantastic weekend getaway in the mountains! quiet neighborhood with stunning night time views of the stars. such a cozy cabin, very clean, linens provided, nice property with a little fire pit too! very friendly host, easy to contact and pleasant. "
United States
Jennifer
Cozy Updated Log Cabin with Mountain Views close to Monadnock

Ski-in/Ski-out Condo with central air -Seasons on Mt. Snow

West Dover
9.8 out of 10, Exceptional, (97)
"It is so clean and well maintained. It is ski in ski out. Would stay again in a minute "
United States
Dan P.
Ski-in/Ski-out Condo with central air -Seasons on Mt. Snow

Beautiful Townhouse In Turners Falls!

Turners Falls
9.8 out of 10, Exceptional, (142)
"Very comfortable place for my wife and I. Location is ideal for exploring the Berkshires and points north and south. We’ll likely be back for another stay."
United States
Mark E.
Beautiful Townhouse In Turners Falls!

Wellness Getaway with a Personal Sauna, and Private River Beach!

2.0 star property
Newfane
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is AU$387
includes taxes & fees
14 Dec - 15 Dec
Wellness Getaway with a Personal Sauna, and Private River Beach!

Two-story, dog-friendly house with wood fireplace

Wardsboro
8.4 out of 10, Very good, (29)
"House was awesome! Fit a large group well! Would recommend for sure!"
United States
Maxwell P.
Two-story, dog-friendly house with wood fireplace

Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking

Whitingham
10.0 out of 10, Exceptional, (31)
"The house was so well stocked and very child friendly. So many personal touches that made us feel at home and comfortable. Would definitely stay again!"
United States
Brittany M.
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking

Waterfront Cottage on Scenic Sportsman Pond

Fitzwilliam
9.6 out of 10, Exceptional, (44)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
United States
Cathy M.
Waterfront Cottage on Scenic Sportsman Pond

Luxury ADA Unit - 101

Wilmington
Luxury ADA Unit - 101

Private 6 bedroom Chalet 5min to Mt Snow

Dover
9.8 out of 10, Exceptional, (14)
"Great stay and successful bachelor party, host was very accommodating with check-in & check-out timing. Several phenomenal golf courses within 10 minutes of the property, gorgeous views! "
United States
Nick B.
Private 6 bedroom Chalet 5min to Mt Snow

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Walpole
10.0 out of 10, Exceptional, (50)
"We had a very lovely stay. "
United States
mary c.
The price is AU$842
includes taxes & fees
10 Dec - 11 Dec
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Inviting mountain view home with game room, balcony & W/D

West Dover
9.0 out of 10, Wonderful, (9)
"Booked this place for my wife’s birthday with our cousins and this place was perfect. The location was great, check in was super easy, all the amenities were present and all the bedrooms and bathrooms were super clean!Super minor (and only) 2 downsides were that the fan in the main room was broken but we were told that the property manager was trying to fix it, and the vacuum wasn’t working which made cleaning the floors a little difficult. "
United States
Abhijit A.
Inviting mountain view home with game room, balcony & W/D
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 Chesterfield Hotel Reviews

Find out more about Chesterfield

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$308 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 are some of the best holiday rentals that Chesterfield has to offer?

Beautiful Custom Built Timber Frame Home, Sleeps 11: This holiday home rental outside of Chesterfield is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Spofford Lake. While here, Asbury United Methodist Church and Pisgah State Park are other places worth a visit.

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.