Holiday houses in Hampshire County

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Top-rated holiday rentals in Hampshire County

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Guest favourite

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!

8 – 15 Sept

$1,541 AUD total

Guest favourite

Cottage in Petersham

4.99 out of 5 average rating, 149 reviews

Cider House Cottage

Antique guest cottage on a country farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub.

20 – 27 Dec

$1,770 AUD total

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 June

$1,573 AUD total

Guest favourite

Guest suite in Sunderland

5.0 out of 5 average rating, 143 reviews

Bright private suite minutes to Five College area

Welcome to our bright, newly renovated suite in the historic Elihu Smith home, built in 1847. Centered on historic S. Main Street in Sunderland, we are minutes from UMass, Amherst, Hadley, Deerfield, and located on the local bus route connecting directly to UMass and Amherst. Ideal for stays of any length of time, for business or pleasure during any time of the year and walking distance to the Millstone market, as well the Bridgeside Café. Suite is professionally cleaned between each stay.

29 Aug – 5 Sept

$1,268 AUD total

Guest favourite

Guesthouse in Northampton

4.92 out of 5 average rating, 240 reviews

Large Studio – Walk to Town

IMPORTANT: Please read the full description about the eco-friendly policy before inquiring and click the "CONTACT HOST" button, rather than make a reservation. I will respond very quickly to your request. Thank you for your consideration! A unique studio, loft-like, surrounded by beautiful gardens, a short walk to downtown and Smith College; perfect for visiting the five colleges, attending weddings, graduations, workshops, writing and research; close to hiking and bicycle trails.

24 – 31 Jan

$1,692 AUD total

Guest favourite

Apartment 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 Sept – 3 Oct

$1,493 AUD total

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

$1,404 AUD total

Guest favourite

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.

23 – 30 Mar

$1,785 AUD total

Guest favourite

Guest suite in Amherst

4.95 out of 5 average rating, 111 reviews

Bright, peaceful suite in great location!

This comfy in-law apartment is on a side street in South Amherst, near a main bus line, just blocks away from Hampshire College and 2 miles from downtown Amherst, Amherst College & UMass. Fantastic Cali-Mex and Salvadorian restaurants a 3 minute walk, as are a great pub and pizza shop. The fully-furnished apartment has air conditioning, blackout shades and plenty of space to stretch out and relax. All areas are for guest use only (no shared spaces) with private entrance.

19 – 26 June

$1,441 AUD total

Guest favourite

Apartment in Plainfield

4.97 out of 5 average rating, 238 reviews

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

2 – 9 Mar

$1,475 AUD total

Guest favourite

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.

20 – 27 Feb

$1,375 AUD total

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 Sept – 4 Oct

$1,186 AUD total