Photo by Heather Beaudry

West Chesterfield Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Vacation Rentals in West Chesterfield

Owl's Nest Treehouse
Property grounds

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (7)
"Treehouse was just as the pictures and description portray. It was clean, quiet and peaceful. My wife and I stayed at the Owl's Nest Treehouse for just a quick one night get away. It was the perfect spot for some quiet time alone and a soak in the hot tub. The check in process was as simple as it gets, and the owners were very responsive to the few questions we asked. For dinner we went to Springfield VT (about a 30 min drive). You can probably find something a little closer, but Alstead...
The price is CA $378
CA $461 total
includes taxes & fees
Sep 2 - Sep 3
Owl's Nest Treehouse
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.4 out of 10, Exceptional, (26)
"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. "
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Interior

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (6)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.
Terrace/patio

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

9.6 out of 10, Exceptional, (8)
"The house was clean, nicely decorated, comfortable and all the amenities we needed! "
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Property grounds

Beautiful Lodging at Mount Snow with Hot Tub on Deck

9.4 out of 10, Exceptional, (41)
"Real Vermont feel. Pretty and nice quiet neighborhood!"
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (35)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is CA $160
CA $276 total
includes taxes & fees
Sep 7 - Sep 8
Lovely 2nd Floor Apartment
Downtown Hot Tub Escape
Fridge, microwave, oven, stovetop

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (17)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is CA $315
CA $554 total
includes taxes & fees
Sep 3 - Sep 4
Downtown Hot Tub Escape
Seasons On Mount Snow - Ski-in/Ski-out
Indoor pool, a heated pool

Seasons On Mount Snow - Ski-in/Ski-out

9.8 out of 10, Exceptional, (172)
"Wonderful host / fantastic location "
Seasons On Mount Snow - Ski-in/Ski-out
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

10.0 out of 10, Exceptional, (5)
"Besides it being a *bit* cold, our stay was great! Very close to Brattleboro and a bunch of other walkable towns. Great hiking areas. The yurt was so cute and had pretty much every cooking supply you could need. Will be back again in warmer weather! :)"
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

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

8.6 out of 10, Excellent, (56)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Jacksonville Cabin w/ Wraparound Deck & Views
Dining

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (34)
"Was in town for a race with friends. Great base camp for before and after on an amazing property "
Jacksonville Cabin w/ Wraparound Deck & Views
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Fridge, microwave, oven, stovetop

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

10.0 out of 10, Exceptional, (6)
"Nice in all respects,"
The price is CA $612
CA $1,190 total
includes taxes & fees
Aug 31 - Sep 1
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Beautiful Custom Built Timber Frame Home, Sleeps 11
Smart TV, fireplace, DVD player, table tennis

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (106)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (58)
"We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything."
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Outdoor spa tub

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

9.0 out of 10, Wonderful, (44)
"We enjoyed our stay at the Blue House. Its size and location cannot be beat when it comes to group trips. We will be back!"
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Charming 1-bedroom condo in delightful Dover
Fridge, microwave, oven, stovetop

Charming 1-bedroom condo in delightful Dover

10.0 out of 10, Exceptional, (1)
"The place was nice. It was clean, lots of supplies were provided, and it was in a great location. The host contacted me the day before, letting me know that the wifi was out, and the technician was unavailable until the next week. I was appreciative of the heads up. Unfortunately, the TV was unusable without wifi, no option to watch local channels. Cellular (Verizon) data was non-existent throughout the majority of daytime hours. Despite this smallish issue, I would stay here again! "
The price is CA $147
CA $278 total
includes taxes & fees
Sep 7 - Sep 8
Charming 1-bedroom condo in delightful Dover
Family Friendly Hilltop House In Putney Vermont
Property grounds

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is CA $268
CA $469 total
includes taxes & fees
Sep 13 - Sep 14
Family Friendly Hilltop House In Putney Vermont
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Fridge, microwave, stovetop, coffee/tea maker

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

10.0 out of 10, Exceptional, (47)
"A dream Vt. property, peaceful and scenic, with no worries"
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

9.4 out of 10, Exceptional, (16)
"Highly recommend clean beautiful stay!"
The price is CA $51
CA $343 total
includes taxes & fees
Sep 1 - Sep 2
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Wellness Getaway with a Personal Sauna, and Private River Beach!
Sauna

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
The price is CA $186
CA $351 total
includes taxes & fees
Sep 8 - Sep 9
Wellness Getaway with a Personal Sauna, and Private River Beach!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top West Chesterfield Hotel Reviews

Find out more about West Chesterfield

Find out more about West Chesterfield

Everything you need to know about West Chesterfield 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 West Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation 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 West Chesterfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

West Chesterfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in West 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A West Chesterfield vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of West Chesterfield vacation rentals we have selected for you start as low as CA $51 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on West Chesterfield rentals

At Expedia, we put the best West Chesterfield 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 West 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 West Chesterfield 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 West 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in West Chesterfield?

Yes, you can find vacation rentals close to popular sights in West Chesterfield, or you can select a more secluded option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the riverfront in West Chesterfield. Make sure you have time to check out the entertainment choices and theaters during your trip.

What's the top vacation rental that West Chesterfield has to offer?

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. : Visitors like this West Chesterfield vacation home rental. It is located in the mountains and has a fireplace, a patio, and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

What’s there to see and do in West Chesterfield?

Madame Sherri Forest and Connecticut River are a couple of scenic spots to enjoy the outdoors, whereas Actors Theatre Playhouse is one of the cultural attractions. While here, United States Navy Seabee Bridge and Madame Sherris Castle Ruins are other places worth a visit.

What’s a vacation rental in West Chesterfield like?

Vacation rentals are private properties you can stay in for several days or longer in West Chesterfield. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.