Chesterfield Vacation Home Rentals from CA $279: Search Top Private Vacation Homes for Rent

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Our top choices for Chesterfield vacation homes

1. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Anonymous traveller

CA $594 total

includes taxes & fees

Sep 13 - Sep 14

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

Easthampton Ma.

Paula

CA $390 total

includes taxes & fees

Sep 14 - Sep 15

3. Lovely 2nd Floor Apartment

Greenfield

Christa B.

CA $279 total

includes taxes & fees

Sep 13 - Sep 14

4. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

CA $297 total

includes taxes & fees

Sep 13 - Sep 14

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

Sherwood Forest

William C B.

CA $400 total

includes taxes & fees

Sep 16 - Sep 17

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

Sherwood Forest

Sharon K.

CA $522 total

includes taxes & fees

Sep 14 - Sep 15

7. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

maureen

CA $505 total

includes taxes & fees

Sep 14 - Sep 15

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

Sherwood Forest

Frank M.

CA $570 total

includes taxes & fees

Sep 15 - Sep 16

9. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

CA $460 total

includes taxes & fees

Sep 13 - Sep 14

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

Chicopee

Nicholas B.

CA $733 total

includes taxes & fees

Oct 7 - Oct 8

11. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

CA $930 total

includes taxes & fees

Sep 14 - Sep 15

12. Spacious 5BR w/ Hot Tub & Games

Colrain

Staci M.

CA $907 total

includes taxes & fees

Sep 14 - Sep 15

13. 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.

CA $805 total

includes taxes & fees

Sep 21 - Sep 22

14. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Ann C.

CA $731 total

includes taxes & fees

Oct 13 - Oct 14

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Top Chesterfield Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"The one bedroom room was spacious, comfortable, and clean. Everything was provided in the kitchen. The living area was roomy and comfortable. This experience was much better than the last time I stayed. The staff were polite, friendly, and very helpful."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good

"Stayed overnight for an event at tanglewood, and there’s so much to love about this hotel! Lobby is modern and comfortable, room was a queen suite. The beds were very comfortable and room was immaculately clean. The room could use more electrical outlets, and lighting. The only issue I had was the breakfast was served from 6-10 am on a weekend. By 10, the breakfast area was completely closed up, and all trash cans in the dining area were overflowing. There was one staff member taking out trash, and all the tables were dirty or sticky. It would have been nice to get a muffin or something with coffee to head out for the day. Overall, a great stay, would recommend!"

Hampton Inn West Springfield

10/10 Excellent

"I always love staying here when I visit Springfield! The front desk staff are consistently friendly, welcoming, and helpful, which really makes a difference. The rooms are a little dated, but they’re spacious, clean, and have everything I need for a comfortable stay. The breakfast also has a great variety of options, and parking is always easy to find. I also love that they have snacks available at the front desk—perfect when you need a little something after a long day. Overall, this is definitely one of my go-to places to stay when I’m in the area!"

Comfort Inn & Suites Hadley - Amherst

8/10 Good

"Room was OK, the room we stayed in on the road in Winchester, VA, same brand, was nicer but cost $178.78 less per day. We had a 3 day stay in Hadley. The GM took advantage by adding $120.90+ to the room rate on days 2 & 3. Highway robbery! He offered no excuse when challenged, nothing but we can charge anything we please, you can like it or lump it."

Find out more about Chesterfield

Chesterfield Vacation Homes information

Number of reviews	369
Accommodation	155 Vacation Homes
Lowest Price	CA $279
Highest Price	CA $930

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Check prices for these dates

Our top choices for Chesterfield vacation homes

1. Charming, updated 3 bedroom farmhouse farm stay.