Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

10.0 out of 10, Exceptional, (1)
"My family and I had the most wonderful stay at this beautiful Townshend, VT home! It was not only spotless and cozy, but also perfectly pet-friendly—Julie truly thought of everything. Both our family’s and our pet’s needs were taken care of, which made the experience even more special.Julie’s communication and care were outstanding, and every detail in the home showed thoughtfulness. We felt completely at home and can’t wait to return. Highly recommend this property for anyone looking for a...
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

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

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$576
includes taxes & fees
8 Oct - 9 Oct
Owl's Nest Treehouse

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

10.0 out of 10, Exceptional, (7)
"Beautiful property and great a host! My boys loved getting up early and fishing into the night! Perfect get away from the hustle and bustle of every day life. If you love nature this is a great place. Lots to explore! We had a GREAT also caught some good size BASS. Definitely will be back again. Thanks tons, The Gallant Family "
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

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

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (37)
"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$346
includes taxes & fees
5 Oct - 6 Oct
Lovely 2nd Floor Apartment

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$435
includes taxes & fees
7 Oct - 8 Oct
Wellness Getaway with a Personal Sauna, and Private River Beach!

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

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

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

8.6 out of 10, Excellent, (34)
"Quite secluded clean comfy cabin We enjoyed it very much. Very close to the things we wanted to do."
Bright three-level home with water views, jetted tub, firepit, and pool table

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

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (41)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

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

Waterfront Cottage on Scenic Sportsman Pond

9.6 out of 10, Exceptional, (44)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
Waterfront Cottage on Scenic Sportsman Pond

Beautiful, private log cabin with huge, relaxing screened porch

10.0 out of 10, Exceptional, (39)
"The spot was amazing and everything was exactly what we wanted. "
Beautiful, private log cabin with huge, relaxing screened porch

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

10.0 out of 10, Exceptional, (6)
"We had a magical time at the yurt! Very sweet and rustic but comfortable. Great secluded location but close enough to restaurants and Brattleboro. We will definitely be back. "
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is NZ$439
includes taxes & fees
2 Nov - 3 Nov
Family Friendly Hilltop House In Putney Vermont

Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

10.0 out of 10, Exceptional, (39)
"Absolutely gorgeous mountain view, beautiful cabin, fully stocked kitchen, loved the hiking trails! Owners thought of every little detail to make it feel like home away from home. "
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

10.0 out of 10, Exceptional, (13)
"Loved the area"
The price is NZ$386
includes taxes & fees
27 Oct - 28 Oct
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (20)
"Nice house in a nice location. "
The price is NZ$729
includes taxes & fees
27 Oct - 28 Oct
Downtown Hot Tub Escape
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 Chesterfield Hotel Reviews

Find out more about Chesterfield

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, 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 NZ$346 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?

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC: This holiday home rental outside of Chesterfield is located on a river, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. You can relax into your holiday with a garden and a selection of games.

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, Asbury United Methodist Church and Pisgah State Park 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.