Search Vacation Homes in Chesterfield

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Chesterfield

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is SAR 447
SAR 583 total
includes taxes & fees
29 Jun - 30 Jun
Deluxe Queen Room with 2 Queen Beds

Cozy Home in Holyoke with 3 bedrooms

9.8 out of 10, Exceptional, (6)
"Wonderful stay. Veronica was so kind and super responsive. The house was a great size and have everything we needed. We stayed there with 2 adults and 2 toddlers under 3. It was plenty of space. And a great location to all the area had to offer, museums, fun restaurants in North Hampton, etc. Would definitely stay again. "
The price is SAR 488
SAR 1,207 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Home in Holyoke with 3 bedrooms

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (57)
"We had a wonderful time and loved the house! We will definitely be back!"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (32)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Spacious Private Retreat Near Holyoke State Park!

10.0 out of 10, Exceptional, (7)
"We stayed for a guys hunting trip and the place was what we needed after a long day"
Spacious Private Retreat Near Holyoke State Park!

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

10.0 out of 10, Exceptional, (24)
"Beautiful property with great quality towels, furniture, and amenities. Great views and great location. Would be happy to stay again. "
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (127)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Berkshire Lake at the Pillow, and EV!

9.4 out of 10, Exceptional, (15)
"Had a lovely time at this lake house. The lake access was a plus and the house was well stocked with water accessories and food items. Otis is a short distance from Lee and Lenox providing easy Berkshire access. Having a garage to park the car in was also nice. The only downside is the relatively poor condition of the driveway / shared road the house is on. The neighborhood is made up of single lane dirt roads that have suffered from some wet weather. All in all would definitely recommend."
Berkshire Lake at the Pillow, and EV!

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

10.0 out of 10, Exceptional, (65)
"This was our second time staying here and we had a great time!"
The price is SAR 675
SAR 1,048 total
includes taxes & fees
23 Jun - 24 Jun
The Creation Station is a cozy place so make yourself at home.

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (25)
"Easy stay, good location for us. Would stay again. "
The price is SAR 436
SAR 755 total
includes taxes & fees
5 Jul - 6 Jul
Lovely 2nd Floor Apartment

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
9.6 out of 10, Exceptional, (4)
"A great place for a family stay in downtown Amherst. "
The price is SAR 1,006
SAR 1,874 total
includes taxes & fees
29 Jun - 30 Jun
Charming 4Bds+1crib house with patio Amherst Center

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

10.0 out of 10, Exceptional, (2)
"Amazing house"
Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (76)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site

1840's Whaling Captain's Farm Estate, 6-10 guests

10.0 out of 10, Exceptional, (3)
"Such a beautiful home and property. We had a great time exploring during the day and spending time together at night. Sunsets over the pond are particularly lovely and the screened in porch and sitting around a fire in the chiminea outside are the perfect spots for a cocktail. We look forward to our next visit!"
1840's Whaling Captain's Farm Estate, 6-10 guests

Charlemont Retreat on Chickley River w/ EV Charger

9.6 out of 10, Exceptional, (27)
"great place to stay"
Charlemont Retreat on Chickley River w/ EV Charger

Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

10.0 out of 10, Exceptional, (2)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Author Stephen Oates Once Owned

8.0 out of 10, Very Good, (2)
"The house is very close to Amherst on a quiet street. Plenty of room, comfortable beds, and well supplied. We’d stay again! "
The price is SAR 821
SAR 1,520 total
includes taxes & fees
23 Jun - 24 Jun
Author Stephen Oates Once Owned

Peace and quiet on the lake

9.6 out of 10, Exceptional, (215)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is SAR 507
SAR 1,367 total
includes taxes & fees
23 Jun - 24 Jun
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
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.
Save an average of 15% on thousands of hotels when you're signed in