Holiday rentals in Southampton

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Top-rated holiday rentals in Southampton

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Guest favourite

Bungalow in Easthampton

4.92 out of 5 average rating, 430 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

15–22 Jul

€ 169 per night

Guest favourite

Guest house 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!

8–15 Sep

€ 135 per night

Guest favourite

Guest suite in Easthampton

4.91 out of 5 average rating, 224 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.

3–10 Nov

€ 178 per night

Guest favourite

Guest suite in Williamsburg

4.98 out of 5 average rating, 230 reviews

Happy Maples!

I am a custom builder and I decided to have some fun building out my own special guest space. Welcome to Happy Maples! The suite is a private 600 sq ft hand crafted studio with private entrance, bath w/shower, large deck w/Adirondack chairs and grill, views of the gardens and 100' from the historic Mill River right behind the house. There is a queen bed and an additional twin memory foam bed available. 12 mins to Northampton, 20 mins to Amherst, Bike trail in back yard. Come for a fun visit!

12–19 Jun

€ 138 per night

Guest favourite

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.

23–30 Nov

€ 123 per night

Guest favourite

Flat 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.

23–30 Mar

€ 157 per night

Guest favourite

Flat in Hadley

4.97 out of 5 average rating, 211 reviews

Sweet Retreat minutes from Northampton & Amherst

Our home is in Hadley, MA which is less than 5 minutes from Amherst and 10 minutes from Northampton. Amherst is home to the flagship campus of University of Massachusetts, Amherst College and Hampshire College. Northampton is home to Smith College and in nearby South Hadley is the campus of Mount Holyoke College. Hadley is known for it's farmlands and open spaces. Northampton is a vibrant arts community that overflows with great restaurants, shops, cafes, music venues and galleries.

26 Sep – 3 Oct

€ 131 per night

Guest favourite

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.

5–12 Oct

€ 106 per night

Guest favourite

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.

27 Sep – 4 Oct

€ 104 per night

Guest favourite

Flat 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.

20–27 Feb

€ 121 per night

Guest favourite

Flat 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).

20–27 Jun

€ 155 per night

Guest favourite

Flat in Northampton

4.96 out of 5 average rating, 278 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!

31 Aug – 7 Sep

€ 155 per night