A stone archway surrounded by lush greenery and trees.

West Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for West Chesterfield holiday rentals

A rustic cabin with a covered porch, a small shed, and outdoor seating.

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

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is NZ$300
includes taxes & fees
29 Oct - 30 Oct
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

2. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is NZ$186
includes taxes & fees
30 Oct - 31 Oct
Cozy Vermont Tiny Home Get Away
A garden with a wooden pergola, purple flowers, and a river view.

3. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is NZ$456
includes taxes & fees
20 Oct - 21 Oct
Family Friendly Hilltop House In Putney Vermont
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

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

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is NZ$500
includes taxes & fees
3 Nov - 4 Nov
Wellness Getaway with a Personal Sauna, and Private River Beach!
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

5. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (12 reviews)
"What an amazing Yurt. The location was so peaceful. The yurt and outhouse was super clean. Hosts were friendly and helpful. I would stay again if in the area."
United States
Troy H.
The price is NZ$267
includes taxes & fees
14 Oct - 15 Oct
Yurt Oasis in the woods of Hinsdale, NH
A wooden interior with a kitchen, bar area, and dining space.

6. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (6 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is NZ$469
includes taxes & fees
25 Oct - 26 Oct
The Studio with a View. Bring your dog, too!
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

7. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is NZ$603
includes taxes & fees
13 Oct - 14 Oct
Vikings Villages Resort - Double Bed Room
A blue house with a porch, a wooden bench, and a door.

8. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.2 out of 10, Wonderful, (10 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is NZ$431
includes taxes & fees
2 Nov - 3 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

9. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is NZ$350
includes taxes & fees
13 Oct - 14 Oct
The Eagles Wing at The CHM - Private Apartment
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

10. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is NZ$403
includes taxes & fees
3 Nov - 4 Nov
Lovely 2nd Floor Apartment
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

11. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (4 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is NZ$868
includes taxes & fees
2 Nov - 3 Nov
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

12. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is NZ$546
includes taxes & fees
26 Oct - 27 Oct
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

13. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is NZ$720
includes taxes & fees
22 Oct - 23 Oct
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A calm lake with a wooden boat on the shore.

14. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is NZ$519
includes taxes & fees
13 Oct - 14 Oct
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A lakeside park with picnic tables and a concrete walkway.

15. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is NZ$145
includes taxes & fees
8 Oct - 9 Oct
2 private mountain RV pads for rent. Full hook ups
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

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

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
The price is NZ$627
includes taxes & fees
7 Nov - 8 Nov
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
A spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.

17. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.4 out of 10, Exceptional, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is NZ$823
includes taxes & fees
21 Oct - 22 Oct
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

18. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (20 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is NZ$771
includes taxes & fees
2 Nov - 3 Nov
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

19. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is NZ$1,161
includes taxes & fees
1 Nov - 2 Nov
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A hallway with a bench, a wall-mounted towel rack, and a door leading to an outdoor area.

20. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (12 reviews)
"Loved this place so much! Adorable spot, quaint but has everything you need. Loved the luxury details. "
United States
Carly L.
The price is NZ$862
includes taxes & fees
2 Nov - 3 Nov
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
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

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

8/10 Good
"The room was VERY small, but it was clean and the bed was comfortable. There is not an attendant or any staff onsite. I had a bit of trouble getting the pet registration taken care of since I booked through a 3rd party. We asked for a 1st floor room since there's not an elevator. When we received our check-in information, we were given a room on the 2nd floor. If we only had to carry backpacks, it might have been fine. However, we had large cases, so it was difficult to drag them up the stairs. Also, if you are an above average size person, know that these rooms are small spaces. The bathroom is barely big enough to turn around in and the shower is tiny."
KERRY 1-night trip
Posted 2 hours ago
Hideaway Inn Mt. Snow

Find out more about West Chesterfield

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our West Chesterfield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up West Chesterfield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in West Chesterfield. Seeing all the best attractions is bound to make you fall in love with West Chesterfield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in West Chesterfield short-term rentals, that won’t be hard to do.

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?

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews: This holiday home rental outside of West 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’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.