Vacation rentals in Pioneer Valley

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Top-rated vacation rentals in Pioneer Valley

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

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!

Dec 5 – 12

€ 132 per night
Guest favorite

Apartment in Greenfield

4.96 out of 5 average rating, 257 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 23 – 30

€ 109 per night
Guest favorite

Guest suite in Northampton

4.86 out of 5 average rating, 438 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.

Dec 21 – 28

€ 110 per night

Popular amenities for Pioneer Valley vacation rentals

Other great vacation rentals in Pioneer Valley

Guest favorite

Guest suite in Northampton

4.86 out of 5 average rating, 347 reviews

Cheery artist's studio in Florence

Aug 15 – 22

€ 104 per night
Guest favorite

Barn in Northampton

4.95 out of 5 average rating, 534 reviews

E. Slate Carriage House

Aug 21 – 28

€ 152 per night
Guest favorite

Apartment in Northampton

4.88 out of 5 average rating, 104 reviews

Elm Suite - Private Bathroom in front of Smith

Nov 12 – 19

€ 140 per night
Guest favorite

Cottage in Petersham

4.99 out of 5 average rating, 146 reviews

Cider House Cottage

Nov 6 – 13

€ 149 per night
Guest favorite

Guest suite in Easthampton

4.96 out of 5 average rating, 399 reviews

Goreytastic Private ApARTment @ the EMC

Aug 15 – 22

€ 101 per night
Guest favorite

Apartment in Northampton

4.96 out of 5 average rating, 303 reviews

The Cottage Room Studio Apartment

Aug 18 – 25

€ 145 per night
Guest favorite

Apartment in Shelburne Falls

4.96 out of 5 average rating, 286 reviews

Annies’ Place by The Bridge of Flowers ~

Jan 4 – 11

€ 110 per night
Guest favorite

Apartment in Williamsburg

4.87 out of 5 average rating, 180 reviews

Studio apartment on route 9, "Inn the Valley"

Mar 26 – Apr 2

€ 142 per night
Guest favorite

Guest suite in Greenfield

4.94 out of 5 average rating, 143 reviews

Pristine Oasis with Private Bath

Nov 10 – 17

€ 75 per night
Superhost

Yurt in Williamsburg

4.87 out of 5 average rating, 173 reviews

magical yurt in the woods. long term discount

May 23 – 30

€ 88 per night
Guest favorite

Guest suite in Northampton

4.98 out of 5 average rating, 225 reviews

Luxurious and Sunny Bedroom Suite!

Jun 17 – 24

€ 171 per night
Guest favorite

Guesthouse in Northampton

4.92 out of 5 average rating, 239 reviews

Large Studio – Walk to Town

Dec 4 – 11

€ 145 per night

Destinations to explore