Chesterfield Holiday Homes from £162: Search Holiday Homes in Chesterfield

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chesterfield holiday homes

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

1. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Nancy M.

includes taxes & fees

18 Oct - 19 Oct

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

2. Lovely 2nd Floor Apartment

Greenfield

Jane P.

includes taxes & fees

18 Oct - 19 Oct

A cozy room with two beds, large windows, and a view of a snowy landscape.

3. The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.

Paula

includes taxes & fees

9 Nov - 10 Nov

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

4. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

includes taxes & fees

3 Nov - 4 Nov

A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

5. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

includes taxes & fees

16 Nov - 17 Nov

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

6. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

includes taxes & fees

28 Oct - 29 Oct

A bedroom with a four-poster bed, a dresser, a chair, and a large window.

7. Steps from Amherst town common, 3 BR charmer

East Village Historic District

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with stainless steel appliances, a granite countertop, and a view into the dining area.

8. Cozy Home in Holyoke with 3 bedrooms

Holyoke

Grant J.

includes taxes & fees

27 Oct - 28 Oct

A hot tub with a string of lights above it, set against a dark night sky.

9. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

includes taxes & fees

28 Oct - 29 Oct

A hallway with wooden flooring, white walls, and a bed in the background.

10. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

maureen

includes taxes & fees

21 Oct - 22 Oct

A house with a porch, a garden with pink flowers, and a stone wall along the road.

11. Big farmhouse in the foothills of the Berkshires

Russell

Dale B.

includes taxes & fees

22 Oct - 23 Oct

A bedroom with a bed, curtains, a bedside table, and a lamp.

12. Townhouse with Pool Table - Renovated w/ King Bed

Chicopee

Nicholas B.

includes taxes & fees

27 Oct - 28 Oct

A dining area with a long wooden table set for six, surrounded by chairs. There are hanging pendant lights above the table.

13. Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

Amherst

Emily Robustelli K.

A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

14. Amherst -NEW - Campus Convenience & Social Privacy

Amherst

Susan N.

includes taxes & fees

5 Nov - 6 Nov

A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

15. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

16. Spacious 5BR w/ Hot Tub & Games

Colrain

Staci M.

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

17. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

includes taxes & fees

16 Nov - 17 Nov

A living room with a sofa, armchairs, a coffee table, and a television.

18. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

includes taxes & fees

28 Oct - 29 Oct

A wooden deck with a table and chairs, surrounded by a white railing.

19. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

includes taxes & fees

18 Oct - 19 Oct

View all properties

Find holiday rentals that suit your style

Private holiday homes

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Chesterfield Hotel Reviews

River Valley Inn

10/10 Excellent

"This is a remodeled and updated classic motel. Knowing that there was no breakfast provided we made use of the microwave and fridge by bring items for our own breakfast. We had the deluxe room and it was super clean and comfy and the owners were very helpful at the check-in with suggestions and the offer of morning coffee in the office. For the area this is a great bargain and we would stay again if we are back in the vicinity."