Chesterfield Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chesterfield Vacation Homes

Lovely 2nd Floor Apartment
Relax in a serene space with a comfortable armchair, console table, and lush greenery.

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is CA $159
CA $276 total
includes taxes & fees
Aug 14 - Aug 15
Lovely 2nd Floor Apartment
Downtown Hot Tub Escape
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and oven, surrounded by dark cabinetry and a wooden countertop.

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (15)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is CA $413
CA $673 total
includes taxes & fees
Aug 10 - Aug 11
Downtown Hot Tub Escape
Timeless Red Sox Retreat w/ Scenic Mountain Views!
Enjoy cooking in this kitchen with a brick fireplace, large island, and modern appliances.

Timeless Red Sox Retreat w/ Scenic Mountain Views!

10.0 out of 10, Exceptional, (23)
"Beautiful property "
Timeless Red Sox Retreat w/ Scenic Mountain Views!
Story Book Lake Front Chateau with Private Beach!
Stunning multi-level space with a grand staircase, exposed beams, and a vaulted ceiling.

Story Book Lake Front Chateau with Private Beach!

10.0 out of 10, Exceptional, (8)
"We had a wonderful stay here over three nights in mid-April. We loved the style and personal touches of the property, and our dog loved how dog friendly it was and especially loved being able to prance around the beach and pull sticks out of the lake. Our visit was fantastic, and we’d happily come back sometime — well worth it!"
Story Book Lake Front Chateau with Private Beach!
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Enjoy meals and games in this kitchen with a central island and pool table.

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

10.0 out of 10, Exceptional, (3)
"Friends and I were in the area for a concert at Tree House Brewing. This house wasn’t far and it is a gorgeous home. Super clean and had all amenities. Would stay here again!"
The price is CA $234
CA $511 total
includes taxes & fees
Aug 13 - Aug 14
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Beautiful Custom Built Timber Frame Home, Sleeps 11
Relax in this inviting living room with a stone fireplace, large windows, and comfortable seating.

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (105)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11
Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi
Dining

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

10.0 out of 10, Exceptional, (1)
"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!! "
The price is CA $214
CA $282 total
includes taxes & fees
Aug 10 - Aug 11
Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi
Cozy cottage tucked away in the woods
Sit by the fire pit surrounded by tall trees in a serene forest setting.

Cozy cottage tucked away in the woods

10.0 out of 10, Exceptional, (43)
"Nice and comfy - loved the decor and the property."
Cozy cottage tucked away in the woods
Charming 4-bedroom Colonial in lovely Keene with WiFi, AC
Relax in this inviting living space with a wooden ceiling, comfortable sofa, and dining area.

Charming 4-bedroom Colonial in lovely Keene with WiFi, AC

10.0 out of 10, Exceptional, (1)
"The home was inviting clean and comfortable. Our inviting, provided us with ample kitchen items, towels, and entertainment in the form of books and extensive library of nostalgic albums and games. There was plenty of parking for four cars in the driveway as well as street parking if needed. The location was perfect for walking into town to enjoy the many restaurants and shops."
Charming 4-bedroom Colonial in lovely Keene with WiFi, AC
Fabulous Mountain Top Retreat - 10 minutes from mount snow!
Relax in this serene space with a bed against the wall, flanked by windows and a cozy seating area.

Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Fabulous Mountain Top Retreat - 10 minutes from mount snow!
A vacation destination in Southern Vermont
Enjoy cooking in this well-lit kitchen with a central island and stainless steel appliances.

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
Countryside, mountain-view house near eagle's nest with patios - dog-friendly
Laundry room with washer and dryer, adjacent to a patio area with outdoor seating.

Countryside, mountain-view house near eagle's nest with patios - dog-friendly

9.6 out of 10, Exceptional, (5)
"Perfect little spot for a ski trip to Stratton!"
Countryside, mountain-view house near eagle's nest with patios - dog-friendly
Hilltop Home with Great Views
Escape to a serene oasis surrounded by lush greenery and a tranquil river view.

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"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...
Hilltop Home with Great Views
Bright three-level home with water views, jetted tub, firepit, and pool table
Kitchen features a central island, dining area, and window with outdoor views.

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

8.4 out of 10, Very good, (29)
"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"
Bright three-level home with water views, jetted tub, firepit, and pool table
Charming Waterfront Log Cabin
Cozy cabin interior with a central staircase, living area, and bedroom, perfect for relaxation and casual gatherings.

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (40)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
Family Friendly Hilltop House In Putney Vermont
Escape to a serene oasis surrounded by lush greenery and a tranquil river.

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 CA $206
CA $394 total
includes taxes & fees
Aug 18 - Aug 19
Family Friendly Hilltop House In Putney Vermont
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Enjoy cooking in this well-equipped kitchen with a spacious island and ample storage.

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

10.0 out of 10, Exceptional, (54)
"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
Two-story, dog-friendly house with wood fireplace
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, microwave, and sink.

Two-story, dog-friendly house with wood fireplace

8.4 out of 10, Very good, (29)
"House was awesome! Fit a large group well! Would recommend for sure!"
Two-story, dog-friendly house with wood fireplace
Pet-friendly Farmhouse, near hiking!
Relax in this inviting living room with a round coffee table, plush armchairs, and a cozy sofa.

Pet-friendly Farmhouse, near hiking!

Pet-friendly Farmhouse, near hiking!
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Relax in a serene outdoor space with three Adirondack chairs surrounding a planter.

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

9.8 out of 10, Exceptional, (17)
"Very clean, well equipped and thoughtfuly supplied. An extra bonus were the great assortment of books, games, movies, and puzzles available. A great deal of experience and generosity went into choices made, and it was much appreciated. "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"We were completely stunned with how wonderful this hotel was from top to bottom. The staff was very friendly and accommodating (they let us have a 1 hour late check out with no charge), the breakfast was fantastic (best I’d ever had in a hotel that offers it free), it was extremely clean, and the attention to detail was amazing. This hotel should have reviews over 9.0!"
tammy 1-night trip
Posted 1 day ago
Best Western Plus Keene Hotel