Chesterfield Vacation Rentals

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Vacation Rentals in Chesterfield

Charming Waterfront Log Cabin
Interior
Charming Waterfront Log Cabin
9.8 out of 10, Exceptional, 27 reviews
"This cabin is so wonderful. The linens are exquisite and the beds are super comfortable. It is decorated so cute. There is everything you need! My favorite activity was sitting in the wooden rocking chair on the front porch each morning, drinking coffee, listening to nature (frogs, fish), and watching the lovely pond (which is so big it should be called a lake!) The owner responded to all my questions within minutes. You can even have pizza (regular AND gluten free) delivered!! If you visit, you...
Charming Waterfront Log Cabin
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, 25 reviews
"I’m forever overjoyed with the way people transform small spaces and this cabin is on point! I never even knew the lake was right behind the place! How my dog and I enjoyed our daily walks along the lake road. The lake is a paddlers paradise. Most days I was the only one out there. It IS cabin living so you’ll have some occasional hard water experiences and the fyi g insects are hatching now so they like to visit. Gratefully my dog loves to eat them. Enjoy.! We loved it and will be back for...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Lake
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, 9 reviews
"The grounds were well kept. The house was remodeled and very clean. Lots of room. Equipped with everything you would need. Quiet. Owners were awesome to deal with and easy to get ahold of. I would definitely recommend people to stay there. "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Fridge, microwave, stovetop, coffee/tea maker
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, 22 reviews
"This property is fairytale cute, so welcoming and relaxing. We had a beautiful stay in Vermont thanks to this location. And there were surprise puppies on site!!!!! Honestly this was the kind of trip that gives you confidence in vacation rentals. Clean, wonderfully decorated, off the beaten path a truly relaxing stay! Go outside at night!!!! We dont have stars like that in the city."
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Cozy Cottage Along Idyllic Green River
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, 35 reviews
"We live in three different states and are usually only all together once a year at the oldest sister’s house. This year we decided to go away together after attending a graduation party. Lots of time to talk and laugh! This house was perfect for that!"
Cozy Cottage Along Idyllic Green River
Salt Water Hot Tub, Family & Pet Friendly, 5 bedrooms, Fire Pit, Volleyball
Property grounds
Salt Water Hot Tub, Family & Pet Friendly, 5 bedrooms, Fire Pit, Volleyball
9.8 out of 10, Exceptional, 9 reviews
"The property was clean and well stocked. The host communicated clearly and was responsive. There were nice touches around the house like clear instructions how to operate the hot tub, fans in each bedroom and plenty of puzzles and games. Our family had a nice time and would recommend this property."
Salt Water Hot Tub, Family & Pet Friendly, 5 bedrooms, Fire Pit, Volleyball
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Exterior
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
10.0 out of 10, Exceptional, 39 reviews
"My husband and I wanted a relaxing few days to get away from our hectic lives. This small cabin was perfect, comfortable, and nicely appointed. Reading a book on the screened in porch with a cup of coffee was my favorite part. It is a quiet place in the woods but close to many small and quaint towns to visit in Vermont. The Newfane Store a few miles down the road was a great place to grab a coffee and meal. I also really appreciate that I could bring my dog. Many thanks for a warm and cozy...
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
A vacation destination in Southern Vermont
Fridge, microwave, oven, stovetop
A vacation destination in Southern Vermont
10.0 out of 10, Exceptional, 60 reviews
"The cabin was adorable. The kitchen had everything we needed. Close to Mount Snow for us to ski. The yard was beautiful, and our pup loved it. We walked to the lake through the woods. The garage entrance was perfect for after skiing and to clean the dog after playing in the yard. It was also very clean."
A vacation destination in Southern Vermont
Spectacular Mountain views with all the amentities nearby
1 bedroom, iron/ironing board, free WiFi, bed sheets
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, 41 reviews
"The property was exactly what I was expecting. Check-in was simple and the property was very clean."
Spectacular Mountain views with all the amentities nearby
Downtown Hot Tub Escape
Property grounds
Downtown Hot Tub Escape
9.6 out of 10, Exceptional, 4 reviews
"We had a work get together and it is was perfect. There was a nice spot outside to socialize, and all of the sleeping areas were very comfy. Great stay."
The price is CA $254
CA $482 total
includes taxes & fees
Jun 25 - Jun 26
Downtown Hot Tub Escape
Waterfront Cottage on Scenic Sportsman Pond
Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, 35 reviews
"Had a wonderful weekend kayaking and fishing. Very private and quiet. Great relaxing spot in nature"
Waterfront Cottage on Scenic Sportsman Pond
Jacksonville Cabin w/ Wraparound Deck & Views
Fridge, microwave, stovetop, dishwasher
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, 23 reviews
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Family Friendly Hilltop House In Putney Vermont
Exterior
Family Friendly Hilltop House In Putney Vermont
9.6 out of 10, Exceptional, 50 reviews
"The house was excellent and the view of the pond was amazing! But what we appreciated the most was Michele's help and communication about the snowstorm that was set to hit the area. She had excellent info and advice and was able to move our stay up a day so we could stay ahead of the storm. We had a great trip to Vermont and very much appreciate her help!"
The price is CA $300
CA $499 total
includes taxes & fees
Jun 25 - Jun 26
Family Friendly Hilltop House In Putney Vermont
Hilltop Home with Great Views
DVD player, books
Hilltop Home with Great Views
9.2 out of 10, Wonderful, 12 reviews
"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...
The price is CA $274
CA $467 total
includes taxes & fees
Jun 30 - Jul 1
Hilltop Home with Great Views
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Fridge, microwave, oven, stovetop
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
6.0 out of 10, 8 reviews
"We loved staying in the Newfane home! I was a bit worried at 1st from reading the reviews but it was great. The house was nice and cozy. The sauna and steam tub were AMAZING. We really enjoyed the quiet and we were so close to such great restaurants. We would love to come back!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Fridge, microwave, stovetop, coffee/tea maker
Cozy Falls Brook Cabin: Hike & Swim On-Site!
10.0 out of 10, Exceptional, 4 reviews
"What a beautiful clean cabin nestled next to a brook with lots of hiking paths to explore. Centrally located to several ski resorts. Matt was the most excellent host! I look forward to returning during other seasons!"
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Lakefront Orange Vacation Rental - Pet Friendly!
Property grounds
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, 8 reviews
"It’s a wonderful place to stay!!"
Lakefront Orange Vacation Rental - Pet Friendly!
Beautiful Mt area with beautiful scenic views; 6 miles to Mount Snow Ski Resort.
Terrace/patio
Beautiful Mt area with beautiful scenic views; 6 miles to Mount Snow Ski Resort.
9.4 out of 10, Exceptional, 10 reviews
"We loved our stay and would definitely come back."
Beautiful Mt area with beautiful scenic views; 6 miles to Mount Snow Ski Resort.
Cozy cottage tucked away in the woods
Property grounds
Cozy cottage tucked away in the woods
10.0 out of 10, Exceptional, 34 reviews
"Stayed here to celebrate a birthday, hang out with friends, and go to Stratton. The house was amazing. We really enjoyed the record player and relaxing by the wood stove. The property was kept nicely and the home was very clean. The house had all of the standard things that are typically needed. We look forward to staying there again next year."
Cozy cottage tucked away in the woods
Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington
Fridge, microwave, oven, stovetop
Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington
7.0 out of 10, Good, 4 reviews
"We had a great time here, it was clean and spacious. We thoroughly enjoyed the multiple living areas and the outdoor space."
Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington
Don't see what you're looking for?
See all available properties in Chesterfield
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.

Chesterfield Vacation Rental Travel Info

Number of vacation rentals
3
Known landmarks
Pisgah State Park, Actors Theatre Playhouse and Spofford Lake
International airports
Boston, MA (BOS-Logan Intl.) and Manchester, NH (MHT-Manchester-Boston Regional)

Other types of properties in Chesterfield you may be interested in

Colonial Motel And Spa
Exterior
Colonial Motel And Spa
3.0 star property
6.8 out of 10, 1,002 reviews
"The room was dated but very clean. Customer Service was 5 stars checking in and out. Breakfast was gone in 30 minutes of opening.😐"
The price is CA $134
CA $148 total
includes taxes & fees
Jun 24 - Jun 25
Colonial Motel And Spa
The Covered Bridge Inn
Concierge desk
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very good, 1,001 reviews
"Clean room, comfortable bed, hot shower...all I needed! "Breakfast" was underwhelming. "
The Covered Bridge Inn
Hampton Inn Brattleboro
Lobby
Hampton Inn Brattleboro
2.5 star property
8.4 out of 10, Very good, 911 reviews
"Good stay, per expectations, staff very good"
The price is CA $161
CA $177 total
includes taxes & fees
Jun 23 - Jun 24
Hampton Inn Brattleboro
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.

Everything you need to know about Chesterfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield vacation rentals we have selected for you start as low as CA $254 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 vacation 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 vacation.

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 vacation rental in Chesterfield?

Yes, we offer vacation rentals near top sights in Chesterfield, or you can select a more secluded option if you'd like a relaxing place to stay. Chesterfield is known for its shopping and restaurants.

What are some of the best vacation home rentals in Chesterfield?

Charming Waterfront Log Cabin: This vacation home rental outside of Chesterfield is located on the waterfront and has a garden, a barbecue grill, 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 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 larger area.

What are vacation rentals like in Chesterfield?

Vacation rentals are private accommodations you can stay in for several days or more in Chesterfield. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for small groups.

Recent reviews of Chesterfield properties
Expedia verified reviews

Latchis Hotel

Latchis Hotel

5/5 Excellent
"Beautiful classic hotel!"
A verified traveller stayed at Latchis Hotel
Posted 2 days ago
Latchis Hotel