Vacation rentals in Southampton

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Southampton

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Bungalow in Easthampton

4.92 out of 5 average rating, 422 reviews

The Creation Station

Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

Jun 17 – 24

G$31,640 GYD per night
Guest favorite

Guesthouse in Northampton

5.0 out of 5 average rating, 271 reviews

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Jan 24 – 31

G$25,300 GYD per night
Guest favorite

Guest suite in Easthampton

4.91 out of 5 average rating, 221 reviews

The Floating Library: private hiker's hideaway

(formerly "The Nest") Spacious enough for a small family, cozy enough for a couple, a perfect alternative to a hotel, for exploring New England, or holing up to finish that book (reading or writing). TFL is a welcoming above the garage in-law suite with a private entrance, full kitchen, full bath, laundry room, and touches that will make your stay comfortable, unique and memorable. The location is right at the foot the hiking trails of Mt. Tom, a 20 min walk to idyllic downtown Easthampton.

Dec 10 – 17

G$32,339 GYD per night

Popular amenities for Southampton vacation rentals

Stay near Southampton's top sights

Tandem Bagel Company18 locals recommend
Big E's Supermarket9 locals recommend
Antonio's Pizza & Wings7 locals recommend
Nonotuck Park4 locals recommend
Small Oven Bakery25 locals recommend
Coco and The Cellar Bar29 locals recommend

Other great vacation rentals in Southampton

Guest favorite

Guesthouse in Amherst

4.95 out of 5 average rating, 473 reviews

Cozy get-away!

Nov 19 – 26

G$21,459 GYD per night
Guest favorite

Guest suite in Amherst

4.95 out of 5 average rating, 109 reviews

Bright, peaceful suite in great location!

May 5 – 12

G$19,295 GYD per night
Guest favorite

Apartment in Northampton

4.88 out of 5 average rating, 104 reviews

Elm Suite - Private Bathroom in front of Smith

Mar 3 – 10

G$25,198 GYD per night
Guest favorite

Apartment in Hadley

4.97 out of 5 average rating, 204 reviews

Sweet Retreat minutes from Northampton & Amherst

Sep 13 – 20

G$28,762 GYD per night
Guest favorite

Apartment in Pelham

4.99 out of 5 average rating, 125 reviews

Pelham 2nd floor Apartment

Apr 3 – 10

G$19,412 GYD per night
Guest favorite

Barn in Northampton

4.95 out of 5 average rating, 535 reviews

E. Slate Carriage House

Oct 18 – 25

G$28,960 GYD per night
Superhost

Home in Northampton

4.88 out of 5 average rating, 559 reviews

The Farmhouse - Hot tub eclectic farmhouse 3 br

Jun 5 – 12

G$61,503 GYD per night
Guest favorite

Apartment in Williamsburg

4.87 out of 5 average rating, 180 reviews

Studio apartment on route 9, "Inn the Valley"

Aug 31 – Sep 7

G$27,135 GYD per night
Guest favorite

Guesthouse in Granby

4.99 out of 5 average rating, 699 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

Dec 10 – 17

G$33,877 GYD per night
Guest favorite

Camper/RV in Westhampton

4.88 out of 5 average rating, 80 reviews

AirbytheStream waterfront, private, clean and cozy

Jan 19 – 26

G$18,815 GYD per night
Guest favorite

Guest suite in Northampton

4.84 out of 5 average rating, 25 reviews

Cozy Guest Suite in Northampton

Sep 12 – 19

G$21,075 GYD per night
Guest favorite

Apartment in Easthampton

5.0 out of 5 average rating, 64 reviews

Briggs Cove: Private & Lovely 1st floor apartment

Feb 8 – 15

G$32,044 GYD per night

Destinations to explore