Chesterfield Holiday Rentals from €337: Search Short-Term Rentals

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

Charming Waterfront Log Cabin : This holiday home rental outside of Chesterfield is located on the waterfront, and has a garden, a BBQ and air conditioning 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.

Check Chesterfield holiday rental availability

Holiday Rentals in Chesterfield

"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."

3 bedrooms, travel cot, free WiFi, bed sheets

"We really appreciated the solitude and quiet retreat this cabin offered. "

"Amazing place. Offered everything we needed and more. Very warm and comfortable. Well appointed too. We will be back for a longer stay in 2025. "

"Every need accommodated including a back-up generator! Well appointed kitchen and bathrooms. Very cozy and spacious home inside. Very comfortable bed mattress in master bedroom. Lots of yard for dogs to run free. Nature all around. Lots of books and board games there. Laundry room was a big plus. Remote setting but lots to see and explore within reach. Very lovely stay and hosts were very responsive."

"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...

"Sportsman's Pond and Blueberry Cottage provided the ideal location for disconnecting from the noise and busyness of every day life. The pond was beautifully serene, without outboard motors, jet skis, etc. The fall colors were gorgeous. The hosts provided every sort of watercraft one might want. I kayaked everyday exploring the shoreline and watching for birds. The cottage was well equipped, the bed was comfortable and an assortment of chairs and couches were available for lounging, viewing the...

"Great place, game room provided many laughs. It was clean, nice quite private property. We will stay again"

"We enjoyed our stay. Everything was clean. The only thing I would suggest is checking the stairs to the basement. "

"The property was beautiful--great views, super peaceful, and fabulous hosts. "

includes taxes & fees

27 Nov - 28 Nov

"We loved this property with stunning foliage, hiking trails, and perfect views. The house had everything we needed to accommodate a large group and more with lots of thoughtful touches. Plenty of space, panoramic views, screened in porch, fireplace, pool table, and connected speakers throughout. We have stayed at many different rentals for our annual trip over the years and this one is our new favorite."

"We stayed at the Mountain View for a work field trip. We were celebrating the delivery of several pianos we rebuilt for the Yellow Barn I'm Putney. We spent most of our time outside, but when we came back, it was delightful. This is a beautiful property, very clean, and very cozy"

"Very nice house and property! "

"The house was clean, beds were comfortable and the area is very quiet. The deck was a very nice. Unfortunately the gas fireplace didn’t work. It actually looked like there were pieces missing which was disappointing because it was the final reason I chose this house. Also, there’s a dishwasher but no dish soap provided. The water pressure in the shower is a little more than a trickle. "

"House is great, we had a large group. 2 living rooms, one with tv one without was a nice separation. To give some details on the layout, the bunk bed rm and twin room are off the living room on the main level, all other bd rooms are on the second floor. From the parking area to the main front door there are 31 steps.... not sure that was stated anywhere but hopefully everyone reads this review. I will stay here again if my group size demands it, it's close to mt snow, pretty secluded overall...

4 bedrooms, desk, iron/ironing board, Internet

"Stayed here with my brothers and cousins.. had a great time. Close proximity to Royalston Falls and a great hike through the forest "

" The home has everything that you could possibly need. The host was great in checking in to make sure our stay was going well and if we needed anything. The beds were comfortable, the living room spacious and a great place to hang out. The house was spotless. The outdoor area is beautiful and a fantastic place to enjoy the beautiful setting. Best VRBO that I have stayed at, we are hoping to make a return trip. Would highly recommend!"

includes taxes & fees

10 Dec - 11 Dec

"What a wonderful place to stay!! We were in town for my 50th high school reunion, hadn’t been back to the area in 35 years. Our accommodations enhanced a beautiful weekend, and the foliage was the cherry on top! Spacious, clean, tastefully furnished and decorated. Well equipped with every utensil, and kitchen appliance you could need! Comfy bed, great shower & good water pressure too! Secluded and quiet, but very convenient to Bernardston, Northfield and Greenfield as well as I-91. Highly...

"It is a beautiful home with a ton of space (we only had 3 people, but it easily sleeps 6), very clean and well-kept. Our hosts provided everything we needed to make our stay perfect. I also like that the hosts were not overboard with all the rules, as with some other rentals. The hosts were beyond friendly and had excellent communication throughout the whole process. If you are looking for a lovely home with a ton of space to stay while exploring Vermont and Massachusetts, I highly recommend...

"We loved the lake and the location. Very nice lake. My kids loved swimming, kayaks and paddle boats. Lovely dock with gorgeous sunset. House is very rustic. The stairs are steep and slippery. Could use a handle rail for safety and may not be appropriate for those with small kids or mobility issues. Beds very small. Screened porch room had some defects in the screen and because of this there were lots of bugs. Otherwise comfortable and very fun. Owners responsive and cabin quite cute and...

"Love this property. We had everything we needed and then some. wasn't exactly sure as to where to put the trash as I don't have email on my phone , therefore I didn't receive the email about the trash and laundry until I got back home. I would rather have been able to text but everything worked out for us, and we had a wonderful, relaxing time."

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Other types of properties in Chesterfield you may be interested in

"The staff are nice "

includes taxes & fees

1 Dec - 2 Dec

"Easiet and nicest place ive stayed in a while"

includes taxes & fees

22 Dec - 23 Dec

"The housekeeping services were excellent and the staff was friendly The facility is a bit old but incredibly clean "

includes taxes & fees

1 Dec - 2 Dec

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, apart-hotels, 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 favorite 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 depends 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 €337 per night. Entering your travel dates in the search wizard you might find 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.

Recent reviews of Chesterfield properties

Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel

5/5 Excellent

"Sat outside for a few minutes at a table and chairs at the fire was awesome. The person at check in was extremely welcoming, cookies in the lobby. People relaxing. Inside looks pretty and clean. Beds are pretty comfy, room is spacious. They accommodated my requests. The little store downstairs is perfect, have snacks, frozen meals, earrings and.. post cards!!!! Only a couple things is that the showers maybe need to be recocked? They look they arent as nice as everything else.Will definitely stay here again. Excited for breakfast. "

A verified traveller stayed at Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel

Posted 2 days ago

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?

Charming Waterfront Log Cabin: This holiday home rental outside of Chesterfield is located on the waterfront, and has a garden, a BBQ and air conditioning 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.

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 Pisgah State Park. Asbury United Methodist Church and Spofford Lake are a couple of places you'll find in the wider area.

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.

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Holiday Rentals in Chesterfield

Check Chesterfield holiday rental availability

Holiday Rentals in Chesterfield

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

Charming Waterfront Log Cabin

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

Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!

Hilltop Home with Great Views

Waterfront Cottage on Scenic Sportsman Pond

Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington

Jacksonville Cabin w/ Wraparound Deck & Views

Family Friendly Hilltop House In Putney Vermont

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

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

Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

Potter's Place | House in Jamaica with mountain views

Expansive 7-BR Chalet 5-min from Mt. Snow

Historic Home w/ Modern Updates on < 4 Acres

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

Spectacular Mountain views with all the amentities nearby

Cozy Cottage Along Idyllic Green River

Cottage on Laurel Lake, Private lake access, picture perfect sunsets

Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

Other types of properties in Chesterfield you may be interested in

Colonial Motel And Spa

Hampton Inn Brattleboro

The Covered Bridge Inn

Find out more about Chesterfield

Recent reviews of Chesterfield properties

Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel

Comfort Inn & Suites Brattleboro I-91

Hampton Inn & Suites Keene

Days Inn by Wyndham Keene NH

The Covered Bridge Inn

Fairfield Inn & Suites by Marriott Keene Downtown

Hampton Inn Brattleboro

The Putney Inn

Holiday Inn Express Keene, an IHG Hotel

Frequently asked questions