Vacation rentals in Southampton

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Top-rated vacation rentals in Southampton

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Guest favorite

Bungalow in Easthampton

4.92 out of 5 average rating, 427 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 16 – 21

$160 per night

Guest favorite

Guesthouse in Northampton

5.0 out of 5 average rating, 272 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!

Dec 28 – Jan 4

$105 per night

Guest favorite

Guest suite in Easthampton

4.91 out of 5 average rating, 222 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.

Jul 22 – 29

$134 per night

Guest favorite

Guest suite in Northampton

4.86 out of 5 average rating, 442 reviews

Separate apt, 1 mile from downtown, 1 guest only

This is a private, clean, comfortable apartment with New pillow top mattress for 1 person with separate entrance in our new home. You will have the space to yourself. We are a mile from downtown near the bike path, the mill river, and Smith college. Private bathroom with a shower; kitchen basics: fridge, microwave, toaster, teapot, pour over coffee. Wifi and smart tv. Sunny with central air in the summer warm and cozy in the winter. Walk or ride a bike to town. We’re located in Village Hill.

Jan 20 – 27

$89 per night

Guest favorite

Home in Williamsburg

4.99 out of 5 average rating, 157 reviews

Hilltown Studio

Stunning 2nd floor studio (limited kitchenette with easy to prepare Breakfast foods provided) close to Northampton, Smith and the Five Colleges, scenic drive to the Berkshires, one mile to the Snow Farm and just minutes to Valley View Farm. Lovely space & private deck overlooking perennial gardens & wildlife wandering by. Perfect stop when traveling through Western Mass, touring local colleges or a trip to enjoy the music, museums and restaurants in the Pioneer Valley and Berkshires.

Mar 24 – 31

$108 per night

Guest favorite

Apartment in Leeds

4.99 out of 5 average rating, 114 reviews

Private Studio for a Sweet Getaway!

We offer a cozy, comfortable, studio apartment located in the heart of the Pioneer Valley right on the bike path, a walk to Look Park and easy access to hiking. We are a 10 minute drive to downtown Northampton with lots of great restaurants and music. Our proximity to Snow Farm, Smith and the other area colleges makes this an ideal overnight spot for parents in town for a brief visit, people attending area workshops and classes or for those looking to stay longer and explore the area.

Nov 1 – 8

$118 per night

Guest favorite

Apartment in Holyoke

4.88 out of 5 average rating, 100 reviews

Spacious Apartment! Easy on & off of I-91 & I-90

Located off of Northampton St. this 2nd floor apartment is close to I-91, I-90 & 391 making for quick & easy travel! There is a beautiful park up the street including a playground, hiking trails and dog park. The Holyoke Mall is located nearby and there is a Walgreens 0.3 miles away. Free street parking. This apartment has one queen bed, two twin beds & a futon in the sun-room if needed for extra guests. This is a private apartment with kitchen, laundry and bathroom all to yourself!

Apr 30 – May 7

$134 per night

Guest favorite

Guest suite in Northampton

4.86 out of 5 average rating, 350 reviews

Cheery artist's studio in Florence

This 2nd floor guest suite in my home has a private entrance via an outdoor set of stairs, full kitchen, and bathroom (with tub but no shower). The studio has an open floor plan including a front room with twin bed and a smaller TV room with futon sofa that can open into a double bed. Originally my art studio, I now offer it for short-term stays. COVID-19 policy. I allow 24 hours between bookings (no same-day turnovers). I request that my guests be fully vaccinated.

Oct 4 – 11

$85 per night

Guest favorite

Guest suite in Easthampton

4.97 out of 5 average rating, 401 reviews

Goreytastic Private ApARTment @ the EMC

Self-contained completely private in-law Edward Gorey inspired artistic apartment at the Easthampton Music Conservatory (right off the Williston Campus.) Romantic, campy, silly, spooky, quirky space with Edward Gorey and original artwork, a micro library including classic TV shows and popular B movies, vintage Nintendo system & oversized beanbags for Nintendo aficionados of all ages. To be clear: entirely self-contained space. Private EVERYTHING. NO shared spaces.

Aug 16 – 23

$87 per night

Guest favorite

Apartment in Northampton

4.98 out of 5 average rating, 646 reviews

Tree Top Suite, cozy downtown apartment

This is an entire apartment, close to downtown. It is on the third floor, so you will have to walk up two flights of stairs. Because there are dormers (peaked areas in the ceiling), especially tall people might feel a little cramped in this space. There is a king size bed in the bedroom, a living area that includes a kitchenette, dining area, seating area and a smart TV with a fire stick, and a large bathroom. Outdoor seating on the front porch is for your use only.

Dec 15 – 22

$93 per night

Guest favorite

Apartment in Easthampton

4.9 out of 5 average rating, 168 reviews

Private Farm 1 BR Apartment, Close to Everything

Our farm is a quiet, 5+ acre haven one mile from the center of Easthampton and 8-12 minutes to Smith College/Northampton. It's a great base from which to explore all the restaurants, cultural and outdoor activities offered in the beautiful Pioneer Valley. The private apartment is on the first level of our rustic farmhouse and offers a kitchenette, living room, queen bedroom and bathroom. (An additional bedroom is also available-see separate listing for 2BR).

Jun 20 – 27

$121 per night

Guest favorite

Apartment in Northampton

4.96 out of 5 average rating, 277 reviews

Bike Path Hideaway Near Smith, Cooley, Northampton

Modern cozy 1BR with living space, private bathroom, private driveway, screened porch, coded door, and inflatable hot tub! Wooded neighborhood. Bike path along river. 5 min. drive to Look Park. 10 min. drive to Northampton. BR has luxury queen bed, single bed, AC. Cozy LR, WiFi, 55" TV, equipped kitchen. Near excellent hikes. A family lives in attached unit so there is some noise, not during sleep hours. Cats have lived here in the past. Great getaway spot!

Sep 19 – 26

$115 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Southampton vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

Guest suite in Williamsburg

4.98 out of 5 average rating, 230 reviews

Happy Maples!

Mar 17 – 24

$110 per night

Guest favorite

Apartment in Hadley

4.97 out of 5 average rating, 211 reviews

Sweet Retreat minutes from Northampton & Amherst

Oct 2 – 9

$100 per night

Guest favorite

Apartment in Williamsburg

4.87 out of 5 average rating, 181 reviews

Studio apartment on route 9, "Inn the Valley"

May 2 – 9

$113 per night

Guest favorite

Guest suite in Amherst

4.95 out of 5 average rating, 110 reviews

Bright, peaceful suite in great location!

Jul 6 – 13

$101 per night

Superhost

Townhouse in Easthampton

4.85 out of 5 average rating, 261 reviews

In style row house with private hot tub/pool table

Jun 12 – 19

$256 per night

Guest favorite

Home in Granby

4.83 out of 5 average rating, 156 reviews

Clean, Spacious 3 BR Half-Duplex on Quiet 4+ Acres

Aug 9 – 16

$134 per night

Guest favorite

Guest suite in Sunderland

5.0 out of 5 average rating, 143 reviews

Bright private suite minutes to Five College area

Aug 29 – Sep 5

$78 per night

Guest favorite

Camper/RV in Westhampton

4.87 out of 5 average rating, 84 reviews

AirbytheStream waterfront, private, clean and cozy

Dec 22 – 29

$78 per night

Show all

Quick stats about vacation rentals in Southampton

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
$70 before taxes and fees

Frequently Asked Questions

Do house rentals in Southampton have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Southampton. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Southampton?
Southampton has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Southampton?
Yes! Work meets play with ease at over 10 vacation rentals in Southampton featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Southampton?
Experience the best of Southampton with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Southampton?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Southampton have wifi?
Absolutely! We offer over 10 house rentals with wifi in Southampton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southampton have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Southampton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southampton have free parking?
Absolutely! We offer over 10 house rentals with free parking in Southampton. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Southampton

Top-rated vacation rentals in Southampton

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Southampton vacation rentals

Stay near Southampton's top sights

Other great vacation rentals in Southampton

Guest suite in Williamsburg

Apartment in Hadley

Apartment in Williamsburg

Guest suite in Amherst

Townhouse in Easthampton

Home in Granby

Guest suite in Sunderland

Camper/RV in Westhampton

Quick stats about vacation rentals in Southampton

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Southampton have air conditioning?

Are there family-friendly vacation rentals in Southampton?

Are there vacation rentals with a dedicated workspace in Southampton?

How much does it cost to stay in house rentals in Southampton?

What are the most popular amenities for House Rentals in Southampton?

Do house rentals in Southampton have wifi?

Do house rentals in Southampton have a kitchen?

Do house rentals in Southampton have free parking?

Destinations to explore