Photo by Heather Beaudry

Search Vacation Homes in Southampton

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 113 Vacation Homes in Southampton with updated reviews, rates, and availability.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is SAR 563
SAR 960 total
includes taxes & fees
27 Dec - 28 Dec
Cozy apartment located in quiet Williamsburg

Massachusetts Vacation Rental w/ Deck

9.6 out of 10, Exceptional, (15)
"Excellent communication with owner, answered all questions immediately via text when we were onsite. Well maintained property with great basement for hanging out as a family. "
Massachusetts Vacation Rental w/ Deck

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

PICON COZY

7.6 out of 10, Good, (54)
"I booked this for my daughter who is looking to relocate to Western Mass from Central Mass and it was perfect for her. The host was extra helpful and accomodating, and while it was a small and simple space, she was very comfortable and cozy. She would definitely stay again."
The price is SAR 282
SAR 639 total
includes taxes & fees
2 Dec - 3 Dec
PICON COZY

Hadley Amherst Location.Explore the Valley Colleges!

10.0 out of 10, Exceptional, (129)
"The house was amazing, clean and comfortable. The area was great and very close to restaurants and shopping. I just can’t say enough good things about our experience. If I could give it more than five stars I would. "
Hadley Amherst Location.Explore the Valley Colleges!

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (95)
"Easy check in, very clean and well stocked with everything needed. I was visiting my daughter at UMass who had to have knee surgery. There was lots of space for her to get around. It was also close to the University which was important for us as well."
The price is SAR 544
SAR 776 total
includes taxes & fees
1 Dec - 2 Dec
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (128)
"Our stay was wonderful. Host was great with communication. We arrived in the evening, all the lights were on and pellet stove running for us. "
The price is SAR 721
SAR 1,330 total
includes taxes & fees
20 Dec - 21 Dec
Big farmhouse in the foothills of the Berkshires

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

10.0 out of 10, Exceptional, (61)
"We needed a pet friendly location to stay for one night. This place is amazing. Very unconventional and much more than I needed for my family of four but I would recommend it highly. The host was very helpful and friendly. The property would be great for an adult birthday or an extended family get together. "
The price is SAR 676
SAR 1,053 total
includes taxes & fees
2 Dec - 3 Dec
The Creation Station is a cozy place so make yourself at home.

Thomas's Cozy Duplex - Centrally Located

8.4 out of 10, Very Good, (8)
"Eunice was great to work with, and the place was fantastic for our family of four going to six flags."
The price is SAR 413
SAR 1,018 total
includes taxes & fees
2 Dec - 3 Dec
Thomas's Cozy Duplex - Centrally Located

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (54)
"The Lakeview Cottage exceeded expectations! My family was visiting from out of state for our daughters’ Cheer Competition and it was the perfect home away from home. Home was clean, Host was very communicative and accommodating, would definitely book again!"
Linny's Updated Lakeview Cottage - Cozy & Modern

Linny’s Cozy Lakeside Family Friendly Home with dock

9.8 out of 10, Exceptional, (17)
"Welcoming and extremely comfortable. We had a wonderful time. Thank you! "
Linny’s Cozy Lakeside Family Friendly Home with dock

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

10.0 out of 10, Exceptional, (33)
"Nestled very quietly in the woods, this elegant home has everything you need for comfort."
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

Lakeside 5-BR Home in Idyllic Berkshires

Lakeside 5-BR Home in Idyllic Berkshires

Pet-Friendly Farmhouse: Cozy with Large Yard

10.0 out of 10, Exceptional, (1)
"House has lots of room and a super nice screened in porch. Plants everywhere add a nice touch. Large fireplace, all upgraded appliances, big eat in kitchen. Property is on a busier road but backyard although clearly still a kind of cluttered farm setting Is quiet. "
Pet-Friendly Farmhouse: Cozy with Large Yard

The Congamond Cottages: Private Lakefront Cottage

8.4 out of 10, Very Good, (5)
"This was the perfect place to stay during the big E. It was very peaceful and helpful during the bustle of the fair. We hope to book again next year."
The Congamond Cottages: Private Lakefront Cottage

Becket Home w/ 3-Season Porch: Walk to Lake Access

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a clean, quiet spot for a nice weekend getaway. "
Becket Home w/ 3-Season Porch: Walk to Lake Access

Fall Berkshires Retreat! Dog friendly, Hot Tub, Hiking, Canoe!

10.0 out of 10, Exceptional, (2)
"Very clean house, smooth access and well stocked kitchen. Great place for me and some friends to have a mini reunion and go to Tanglewood. My dog loved it too! Hot tub was great. "
Fall Berkshires Retreat! Dog friendly, Hot Tub, Hiking, Canoe!
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.
Don't see what you're looking for?
See all available properties in Southampton
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Southampton

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is SAR 563
SAR 960 total
includes taxes & fees
27 Dec - 28 Dec
Cozy apartment located in quiet Williamsburg

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (209)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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.