Chesterfield Holiday Rentals from €139: Search Short-Term Rentals

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

The Jelly Mill-A Peaceful River Retreat : This holiday home rental outside of 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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Our top choices for Chesterfield holiday rentals

Lovely 2nd Floor Apartment

Greenfield

Mary

includes taxes & fees

8 Jun - 9 Jun

Hiking Trails On-site: Cozy Falls Brook Cabin

Brattleboro

sarah

includes taxes & fees

15 Jun - 16 Jun

Owl's Nest Treehouse

Alstead

Garrett B.

includes taxes & fees

2 Jun - 3 Jun

Fridge, microwave, stovetop, coffee/tea maker

Hiking Trails On-Site: Cozy Falls Brook Cabin

Dummerston

Kelsey M.

includes taxes & fees

15 Jun - 16 Jun

John's Mountain Hideaway

Jaffrey

includes taxes & fees

4 Jun - 5 Jun

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Townshend

includes taxes & fees

2 Jun - 3 Jun

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

Hinsdale

Gina M.

includes taxes & fees

8 Jun - 9 Jun

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

Brattleboro

James M.

includes taxes & fees

2 Jun - 3 Jun

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Top Chesterfield Hotel Reviews

The Putney Inn

10/10 Excellent

"Clean room staff very nice Parking a lot nice big parking lot Breakfast okay, they have coffee juices and a good little breakfast"

Hampton Inn Brattleboro

8/10 Good

"This is the best option in the area and we are big fans of the Hilton family of hotels (we stay there exclusively when this is an option). Everything was as expected for a Hampton Inn, including the workout room, layout of the room, and amenities. Five stars for pillows, hot water, and lack of noise. It was really hard getting an early check in, much harder than one would expect given the occupancy. We did end up getting it in plenty of time, which we appreciated. (It seemed like there were challenges with staffing.) We enjoyed our stay and would stay there again."

Hampton Inn & Suites Keene

2/10 Terrible

"I am disgusted by the behavior of the general manager who hung up the phone on me. I paid for my room in FULL for 2 nights but when I arrived the next day (flight was delayed) I was told I couldn’t check in because they had cancelled my room (kept my money) and sold my room to another guest So that means they got to benefit TWICE from one room Cancelled my room and left me stranded with nowhere to stay And when asked for my money back on the phone with manager, she hung up the phone on me I will never book this hotel again"

The Covered Bridge Inn

4/10 Poor

"I don’t know where to begin. The place smelled like cigarette smoke. When I tried to check in I had to ring a bell and was to come back as the front desk staff seemed to all go out to lunch. After finally checking in, the tv didn’t work, the iron is broken and spilled water everywhere when I tried to iron my clothes. The bathroom showers had mold everywhere and I was genuinely afraid to step on the carpet, barefooted or touch anything in the room. I had to put my own bedsheets and pillowcases on the bed and pillows in order to sleep the other night. At night, there’s a door right outside my window that bangs every 45 minutes due to people going in and out to smoke. I was up all night. There were questionable people outside at all times, outside of the place was super dirty and trashy. Had i known this place was like that I wouldn’t have stayed. Needless to say I will not be returning turning and in fact if I could ask for my money back, I would."

Best Western Plus Keene Hotel

2/10 Terrible

"This place is a dump Pretty much a motel Looks and smells dirty The curtains in bathroom are filthy The tub is disgusting and black No pride in the upkeep of this property Dirty walls and carpets Exposed outlets Didn’t even clean our room I only stayed here because Hampton inn was sold out NEVERRR AGAIN I even left a day early because I refused to raid a shower there"

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 €139 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.

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?

The Jelly Mill-A Peaceful River Retreat: This holiday home rental outside of 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 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 Spofford Lake. While here, Pisgah State Park and Chesterfield Town Hall are other places worth a visit.

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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