Vacation rentals in Pioneer Valley

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Top-rated vacation rentals in Pioneer Valley

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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

R2,297 ZAR per night

Guest favorite

Apartment in Northampton

4.98 out of 5 average rating, 354 reviews

Northampton MA Downtown Townhouse close to Smith

Discover the charm of Northampton from our unique Townhouse apartment nestled in a National Register of Historic neighborhood. This is more than just a place to stay. it's an invitation to experience the rich tapestry of vibrant community. 3 minutes walk to downtown Northampton, where you will enjoy from an array of shops, local restaurants, art galleries, cafes, music venues & the Amtrak station. Whether you're here for business or pleasure, you're at the epicenter of culture & convenience.

Feb 1 – 8

R2,619 ZAR per night

Guest favorite

Apartment in Greenfield

4.96 out of 5 average rating, 267 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Apartment: Entrance, bathroom & driveway are all private. Backyard with gas bbq. Kitchenette has microwave, toaster oven, Keurig coffee maker & sink. 2 TV’s one in living room & bedroom. Netflix, Amazon Prime , HBO & Local programs. High speed internet. Bedroom has Queen bed & desk. Apt. Is 2 min's to Rt. 2 Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes.

Jul 24 – 31

R1,993 ZAR per night

Guest favorite

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!

Mar 17 – 24

R2,419 ZAR per night

Guest favorite

Guest suite in Sunderland

5.0 out of 5 average rating, 142 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.

Aug 29 – Sep 5

R1,731 ZAR per night

Guest favorite

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.

Oct 2 – 9

R2,202 ZAR 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

R2,343 ZAR 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

R2,583 ZAR per night

Guest favorite

Guest suite in Amherst

4.95 out of 5 average rating, 110 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.

Jul 6 – 13

R2,184 ZAR per night

Guest favorite

Apartment in Williamsburg

4.87 out of 5 average rating, 181 reviews

Studio apartment on route 9, "Inn the Valley"

A bright and cozy studio apartment on PVTA bus line just outside of Northampton, MA. Skylight, wood floors, kitchen, and full bathroom as well as heat and air conditioning, oriental rugs and unique furnishings. 10 minutes from Northampton center and 20 minutes from Amherst center. Very convenient for all 5 colleges. Five minutes from Snow Farm Art Institute. Two minutes from Valley View Farm. We are meticulous in our cleaning and disinfecting in the face of Covid-19.

May 2 – 9

R2,463 ZAR per night

Guest favorite

Apartment in Northampton

4.98 out of 5 average rating, 643 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

R2,027 ZAR 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

R1,917 ZAR per night