
Vacation rentals in Southampton
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Southampton
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Southampton vacation rentals
Other great vacation rentals in Southampton
Guest favorite

Apartment in Westfield
4.92 out of 5 average rating, 49 reviewsCozy Apartment
DawnRating, 5 stars4 weeks ago
Exceptional Airbnb! Julie was welcoming and responsive, making the check-in process smooth and stress-free. The space was exactly as described—clean, cozy, and well-equipped with everything needed for a comfortable stay. The location was perfect—quiet yet conveniently close to everything you might need. We would absolutely stay here again and recommend it to anyone looking for a relaxing and hassle-free place to stay.
Top guest favorite

Farm stay in Worthington
4.97 out of 5 average rating, 33 reviewsLike sleeping on a cloud
KimberlyRating, 5 stars1 month ago
We loved our stay. The place is pristine and “user-friendly.” Host was easy to work with and communication was super clear.
Top guest favorite

Home in Russell
4.96 out of 5 average rating, 265 reviewsSouth Quarter House
SheilahRating, 5 stars2 weeks ago
We stayed at South Quarter House for a week with our dogs while competing in a national agility event in the area. It was a great and quiet place to stay and rejuvenate before each day’s events.
Top guest favorite

Cottage in Southwick
4.98 out of 5 average rating, 110 reviews4 Kayaks Fire Pit & Lake Views from Hot Tub
LeahRating, 5 stars2 weeks ago
We did a last minute weekend with our 5 and 2 year olds and Catherine’s place was perfect. The bedrooms being upstairs away from the living area meant it was nice and quiet for the kids, they had life jackets in all sizes, and we visited a fun children’s museum 15 mins away. We had a few questions during our stay and Catherine was always quick to respond and super helpful.
Top guest favorite

Home in Williamsburg
4.99 out of 5 average rating, 190 reviewsHilltown Studio
JeffRating, 5 stars2 weeks ago
This was a terrific place, just as described. It is less than a half mile from a decent size road and a few miles from towns, but it feels very rural. Katherine had the space well-stocked and clean. She was extremely accessible and a pleasure to interact with.
Top guest favorite

Cabin in Williamsburg
4.97 out of 5 average rating, 91 reviewsMountain Retreat close to Northampton & Amherst!
KarenRating, 5 stars2 weeks ago
Outside is simply amazing. Beautiful Orchard, running stream, birds everywhere! Inside, so cozy yet roomy. The bed is just perfect. Shower has wonderful water pressure and very adjustable temperature. This home is just beautiful and very relaxing!
Top guest favorite

Apartment in Easthampton
4.97 out of 5 average rating, 72 reviewsPrivate Farm Studio Apartment
ElizabethRating, 5 stars1 week ago
Mindy’s place was great — private and very cozy! We would definitely stay there again.
Top guest favorite

Guesthouse in Easthampton
4.96 out of 5 average rating, 51 reviewsNewly built loft
SueRating, 5 stars2 weeks ago
The many laudatory reviews of Alison and Andrew’s loft tell the truth. As a writer, I’m hesitant to use too many adjectives, but these come to mind: tasteful, idyllic, spacious, thoughtful, spotless, and comfy. The design and décor are extraordinary – from floor to ceiling. The lighting is sublime. Although there’s no kitchen, there’s a microwave, kettle, coffee-maker, toaster, and half-fridge. The allocated parking spot is well-marked and the motion detector lights are a welcome guide. There is one flight of steps to the loft, with a hardy banister. The location is convenient – don’t miss the pastries at nearby Small Oven or breakfast at the Silver Spoon diner. Most of all, Alison and Andrew respect your privacy while being almost instantly attentive to messages. I’m grateful to have found this jewel and hope to come back.
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- Six Flags New England
- TPC River Highlands
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Kent Falls State Park
- Bash Bish Falls State Park
- Brownstone Adventure Sports Park
- Mount Greylock Ski Club
- Brimfield State Forest
- Norman Rockwell Museum
- Dinosaur State Park
- Beartown State Forest
- Mohawk Mountain Ski Area
- Hartford Golf Club
- Bright Nights at Forest Park
- Bigelow Hollow State Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Mount Southington Ski Area
- Brignole Vineyards