Chesterfield Vacation Homes

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Our top choices for Chesterfield holiday homes

1. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Anonymous traveller

HK$3,248 total

includes taxes & fees

31 Aug - 1 Sept

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

Easthampton Ma.

Paula

HK$2,136 total

includes taxes & fees

15 Sept - 16 Sept

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

Sherwood Forest

HK$2,373 total

includes taxes & fees

13 Sept - 14 Sept

4. Lovely 2nd Floor Apartment

Greenfield

Christa B.

HK$1,603 total

includes taxes & fees

27 Aug - 28 Aug

5. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

HK$1,689 total

includes taxes & fees

8 Sept - 9 Sept

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

Sherwood Forest

Frank M.

HK$3,109 total

includes taxes & fees

8 Sept - 9 Sept

7. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

HK$2,862 total

includes taxes & fees

8 Sept - 9 Sept

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

Sherwood Forest

Sharon K.

HK$3,053 total

includes taxes & fees

8 Sept - 9 Sept

9. Cozy Home in Holyoke with 3 bedrooms

Holyoke

Grant J.

HK$3,083 total

includes taxes & fees

8 Sept - 9 Sept

10. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

HK$2,791 total

includes taxes & fees

2 Sept - 3 Sept

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

Chicopee

Nicholas B.

HK$3,742 total

includes taxes & fees

31 Aug - 1 Sept

12. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

HK$5,254 total

includes taxes & fees

26 Aug - 27 Aug

13. Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont

Noah K.

HK$7,371 total

includes taxes & fees

8 Sept - 9 Sept

14. Chef's Kitchen Family Basecamp Amherst

East Village Historic District

HK$5,314 total

includes taxes & fees

31 Aug - 1 Sept

15. Spacious 5BR w/ Hot Tub & Games

Colrain

Maureen A.

HK$5,124 total

includes taxes & fees

26 Aug - 27 Aug

16. 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.

HK$4,564 total

includes taxes & fees

21 Sept - 22 Sept

17. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Ann C.

HK$4,343 total

includes taxes & fees

26 Aug - 27 Aug

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Top Chesterfield Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Clean room. Nice hotel. Great option in the Lenox area."

Quality Inn West Springfield

8/10 Good

"They have definitely been updates since I was there two years ago. They have repainted the building all the way around. You now need your room pass card to get into the conference room where they serve your continental breakfast. Post looks good. Workout room looks good. They keep a good job on housekeeping, but you do have to ask to be serviced because they don’t do it every day. Other than that, it’s an excellent location your food near Kohl’s if you need something more personal all kinds of things so I will give it a thumbs up."

D. Hotel Suites & Spa

8/10 Good

"Front desk could have been friendlier, but the rest of the staff were very friendly. The pool had been closed one day and I when I asked the front desk if they had any additional information (like how long it would be closed), she was a little curt and uninformative. The breakfast staff were phenomenal. A few lights were out in our room and the toilet didn't fill once. But the place had a lot of character. The fitness room could have been opened a little earlier. It didn't open until 8AM."

Inn on Boltwood

10/10 Excellent

"If you like old inns with modern amenities in historic places , this is your place. The beds are comfortable, the restaurant is first rate for breakfast or dinner, and there's a lovely, spacious library with a fireplace for reading or conversation with friends. The front desk staff are universally friendly and helpful, and provide an unlimited number of bottles of Saratoga water, on request. The inn is located alongside a leafy quad that reduces noise from Amherst's main road. Given the inn's age, a guest might experience noise from heavy-footed guests in the room above, but we did not. Noise was not an issue."

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