West Chesterfield Holiday Rentals from NZ$336: Search Short-Term Rentals

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

The Jelly Mill-A Peaceful River Retreat : This holiday home rental outside of West Chesterfield is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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Holiday Rentals in West Chesterfield

"Easy stay, good location for us. Would stay again. "

includes taxes & fees

17 Aug - 18 Aug

"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! :)"

"Real Vermont feel. Pretty and nice quiet neighborhood!"

"What an absolutely charming place!! It was so lovely staying here. This place is exactly what we wanted... a little weekend escape not too far from home, nestled in the woods. Absolutely beautiful. The hosts were so kind, too!"

includes taxes & fees

9 Sept - 10 Sept

"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."

"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!"

"Would recommend if anyone wants a quiet, peaceful getaway."

"Very nice, clean, and great area. We enjoyed it very much!"

"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "

includes taxes & fees

18 Aug - 19 Aug

"Great place just need the fire place to be fixed asap, especially for the winter time"

"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"

"The house was clean, nicely decorated, comfortable and all the amenities we needed! "

"This was the definition of a New England inn!! Super cute and the staff were fantastic! They were so helpful! I would definitely stay here again!! "

includes taxes & fees

15 Aug - 16 Aug

"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! "

includes taxes & fees

8 Sept - 9 Sept

"The folks are SUPER and made me feel very welome"

includes taxes & fees

2 Sept - 3 Sept

Smart TV, fireplace, DVD player, ping pong

"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"

"Highly recommend clean beautiful stay!"

includes taxes & fees

18 Aug - 19 Aug

"We enjoyed our stay at the tiny home!"

"Wonderful host / fantastic location "

Fridge, microwave, stovetop, coffee/tea maker

"A dream Vt. property, peaceful and scenic, with no worries"

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Top West Chesterfield Hotel Reviews

Latchis Hotel

10/10 Excellent

"Excellent location! Clean and good parking. Could have better lighting for reading in room."

Hampton Inn Brattleboro

10/10 Excellent

"Hotel Review: Hampton Inn – A Seamless Stay with Exceptional Service I recently stayed at the Hampton Inn and was thoroughly impressed by the level of service and hospitality from start to finish. From the moment I walked in, the front desk staff made me feel genuinely welcome. Check-in was quick, and they even offered complimentary bottled water and local dining recommendations, which was a thoughtful touch. The room was spotless, well-stocked, and comfortable — exactly what you’d hope for after a long day of travel. The housekeeping team clearly takes pride in their work. I also appreciated the small details, like plenty of charging ports, crisp bedding, and a quiet HVAC system. What truly stood out, though, was the service. Every staff member I interacted with was friendly, helpful, and professional. Whether it was a late-night request for extra towels or early morning coffee in the lobby, they handled everything with a smile and prompt attention. Breakfast was fresh and well-organized, with a good mix of hot and cold options. The dining area was clean and constantly replenished, even during peak hours — another example of the staff going above and beyond. Overall, this Hampton Inn exceeded expectations. It’s a great value with top-tier customer service that rivals more expensive hotels. I wouldn’t hesitate to stay here again or recommend it to anyone traveling through the area."

Mountaineer Inn

10/10 Excellent

"I love staying at the Mountaineer. I stay there every time I go to Vermont. The staff is very friendly and welcoming. Parking is very easy good location, central to many restaurants and other amenities. Very nice coffee bar beautiful pool for swimming. great atmosphere. Love the easy check-inprocess. Everything is digital no keys to worry about."

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$336 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.

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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?

The Jelly Mill-A Peaceful River Retreat: This holiday home rental outside of West Chesterfield is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 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.

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West Chesterfield Holiday Rentals

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Holiday Rentals in West Chesterfield

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

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

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

Beautiful Lodging at Mount Snow with Hot Tub on Deck

Beautiful Lodging at Mount Snow with Hot Tub on Deck

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful River Retreat

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

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

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Cozy Updated Log Cabin with Mountain Views close to Monadnock

Cozy Updated Log Cabin with Mountain Views close to Monadnock

Downtown Hot Tub Escape

Downtown Hot Tub Escape

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

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

Bright three-level home with water views, jetted tub, firepit, and pool table

Bright three-level home with water views, jetted tub, firepit, and pool table

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

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

Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi

Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi

Charming 1-bedroom condo in delightful Dover

Charming 1-bedroom condo in delightful Dover

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

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

Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11

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

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

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

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

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

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

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

Top West Chesterfield Hotel Reviews

Latchis Hotel

Find out more about West Chesterfield

Find out more about West Chesterfield

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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