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West Chesterfield Holiday Rentals

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28 Sept - 29 Sept
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29 Sept - 30 Sept
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3 Oct - 5 Oct
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10 Oct - 12 Oct

Holiday Rentals in West Chesterfield

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

8.4 out of 10, Very good, (58)
"Great location and super cute"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Owl's Nest Treehouse
Property grounds

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (8)
"This place is beautiful! It had everything we needed. The hosts were very communicative and encouraged us to contact them if we had any questions. We stayed at the treehouse to celebrate our 30th anniversary and it exceeded our expectations. I would highly recommend this cozy and quiet retreat."
The price is NZ$581
includes taxes & fees
29 Sept - 30 Sept
Owl's Nest Treehouse
The Jelly Mill-A Peaceful River Retreat
Exterior

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (59)
"Very much off the beaten path, but lets you experience the beauty of Vermont. Quiet and peaceful. A beautiful little property that served our needs perfectly. Would definitely come back."
The Jelly Mill-A Peaceful River Retreat
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, (7)
"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.
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, (42)
"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, (36)
"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 NZ$349
includes taxes & fees
29 Sept - 30 Sept
Lovely 2nd Floor Apartment
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Interior

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

10.0 out of 10, Exceptional, (84)
"A beautiful cabin in the woods. Very clean and a perfect stay."
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Interior

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (224)
"Great house, fantastically well equipped (kayaks, bikes etc). Excellent, very responsive host. View out over the lake is amazing. Really enjoyed our stay. "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
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, (61)
"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
Beautiful Custom Built Timber Frame Home, Sleeps 11
Smart TV, fireplace, DVD player, ping pong

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
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow
Property grounds

Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

10.0 out of 10, Exceptional, (134)
"This was our second time renting this property for a quick ski trip. The property is spacious, and well appointed. It really offers everything you need for a relaxing ski vacation. Love the game room and the space."
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow
Waterfalls-View-Pond. Secluded Vermont Log Cabin at Mount Snow. EV Outlet
Fridge, microwave, oven, stovetop

Waterfalls-View-Pond. Secluded Vermont Log Cabin at Mount Snow. EV Outlet

10.0 out of 10, Exceptional, (81)
"Perfectly clean and welcoming cabin. Comfy beds, great location. Would definitely return. "
Waterfalls-View-Pond. Secluded Vermont Log Cabin at Mount Snow. EV Outlet
A vacation destination in Southern Vermont
Fridge, microwave, oven, stovetop

A vacation destination in Southern Vermont

10.0 out of 10, Exceptional, (71)
"Super comfortable cabin in a great location."
A vacation destination in Southern Vermont
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
The Myrtle House Heated Pool-Hot Tub, Tennis court, Firepit, Sauna, Gym, Hot Tub
Fridge, microwave, oven, stovetop

The Myrtle House Heated Pool-Hot Tub, Tennis court, Firepit, Sauna, Gym, Hot Tub

The Myrtle House Heated Pool-Hot Tub, Tennis court, Firepit, Sauna, Gym, Hot Tub
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, (45)
"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!
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, (177)
"Wonderful host / fantastic location "
Seasons On Mount Snow - Ski-in/Ski-out
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

8.6 out of 10, Excellent, (31)
"The apartment was in a great location to get to the ski lifts. "
The price is NZ$476
includes taxes & fees
30 Sept - 1 Oct
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
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)
"So cute and in such a great area! It was a perfect stay"
The price is NZ$433
includes taxes & fees
6 Oct - 7 Oct
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 NZ$442
includes taxes & fees
29 Oct - 30 Oct
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.
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Top West Chesterfield Hotel Reviews

Colonial Motel And Spa

Colonial Motel And Spa

10/10 Excellent
"Clean and quiet"
Lorie 1-night trip
Posted 4 days ago
Colonial Motel And Spa

Find out more about West Chesterfield

Find out more about West Chesterfield

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

West Chesterfield holiday 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 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 West Chesterfield holiday rentals we have selected for you start as low as NZ$349 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 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 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 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 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 holiday rental in West Chesterfield?

Yes, there are holiday rentals close to the most popular sights in West Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the riverfront in West Chesterfield. Make sure you have time to check out the entertainment choices and theatres during your trip.

What are some of the best holiday rentals that West Chesterfield has to offer?

Lovely 2nd Floor Apartment: This holiday home rental outside of West Chesterfield offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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

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

What’s a holiday rental in West Chesterfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in West Chesterfield. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.