Bed and breakfast vacation rentals in Pioneer Valley

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Top-rated bed and breakfast rentals in Pioneer Valley

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Guest favorite

Farm stay in Southbridge

4.98 out of 5 average rating, 165 reviews

High Grass Farm

Get cozy in front of the fireplace and enjoy a romantic getaway in our beautiful and historic old house. One of the top 16 farm stays in New England! Our 1780's farmhouse has been completely renovated and retains its rustic country feel. Experience early American period life with only a few modern conveniences (e.g. full laundry and 5G wi-fi). Our secluded setting on 19 acres in southern Mass is minutes from I-90 and I-84, and borders CT, Old Sturbridge Village and the Westville recreation area.

Aug 23 – 30

G$39,356 GYD per night

Guest favorite

Home in Wilmington

4.97 out of 5 average rating, 35 reviews

Find your escape at The Coldbrook House, Mt Snow

A beautifully-secluded modern ski home near Mt Snow with 500 feet of private access to the Cold Brook. Exceptionally furnished with custom wood flooring and stone fireplace, Subzero & Wolf appliances, walk-in shower with custom river rock flooring, pool table, shuffleboard, and 7-person hot tub. 10 min to Mount Snow, 30 to Stratton. 5 min to downtown Wilmington and Herriman Reservoir. Perfect for 3-4 families or couples trips. Come enjoy the beauty of Southern Vermont at The Coldbrook House!

Aug 30 – Sep 6

G$236,584 GYD per night

Guest favorite

Cabin in Wilmington

5.0 out of 5 average rating, 56 reviews

Modern Chalet-private deck/firepit/ clubhouse pool

Nestled in the Green Mountains this custom modern chalet is the perfect location for your family vacation! Enjoy the peaceful tranquility, 12 min. from Mt Snow. The private wrap around deck is the place to be for morning sunrise & coffee Located in Chimney Hill, includes outdoor & indoor pool, gym, tennis, basketball cts. Harriman Reservoir & Lake Raponda for kayaking/ swimming & Wilmington restaurants & shopping are close by. The home is pet free & has high speed fiber! Insta @bearlairlodge

Jul 20 – 27

G$133,621 GYD per night

Guest favorite

Cabin in West Stockbridge

4.98 out of 5 average rating, 48 reviews

Modern Cabin near Tanglewood

Welcome to West Stockbridge in the Berkshires! This newly renovated modern cabin is nestled amongst the trees and located just 3 miles from the famous Tanglewood and Kripalu. Right down the street is main street where you can peruse the shops, grab a gourmet coffee, or listen to more music at the Foundry. There are restaurants, hiking trails, waterfalls and lakes less than a mile away. We are 5 minutes from the turn pike for easy directions! Come hang and enjoy all the activity and beauty.

Dec 8 – 15

G$89,286 GYD per night

Guest favorite

Room in Northampton

4.95 out of 5 average rating, 664 reviews

Warm Country Home Minutes from Town

Comfortable, clean, quiet room with a private bathroom. About 10 minutes away from our vibrant little city -- and yet with countryside at the doorstep. Lovely patio, yard, and nearby hiking trails. We love hosting and we take our hosting seriously to make our guests happy. We work hard to make our home clean. We are fully vaccinated against Covid and welcome vaccinated guests for the safety of all. Also, we have dedicated parking for guests and a 20 amp outlet for EVs.

Mar 28 – Apr 4

G$12,043 GYD per night

Guest favorite

Tiny home in Orange

4.92 out of 5 average rating, 311 reviews

The Writer's Retreat: A Sweetwater Stay

Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill.

Mar 28 – Apr 4

G$28,604 GYD per night

Guest favorite

Farm stay in Williamstown

5.0 out of 5 average rating, 13 reviews

Scenic & Relaxing Farm Stay

Cobble Hill Farm is on the site of the nonprofit Education & Rescue Center. The 25 acre farm is an ideal location for families. The location brings lots of space to spread out and privacy all while being just a few miles to Williams College, Mass MoCA, and the Clark Art Institute. Swimming in the summer, a perfect sledding hill for winter and room for leisurely walks among 360 views of the foliage in the fall provide an escape from every day life.

Sep 7 – 14

G$103,596 GYD per night

Guest favorite

Cottage in Williamstown

4.97 out of 5 average rating, 72 reviews

Artistic Nature Cottage

Kalarama Cottage is a newly renovated space in the middle of nature! Make yourself right at home in this quiet, private and peaceful location. The cottage is overlooking a beautiful forested mountain range, with easy access to hiking, biking, and cross-country ski trails right out the door. Kalarama is bright and sunny with stunning views. Come to unwind, enjoy nature, read, meditate or just work remotely from our 23 acre property!

Nov 16 – 23

G$51,233 GYD per night

Guest favorite

Guesthouse in Granby

4.99 out of 5 average rating, 709 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Feb 28 – Mar 7

G$33,786 GYD per night

Guest favorite

Apartment in Dummerston

4.93 out of 5 average rating, 366 reviews

~Serene Barn Retreat~

Peaceful, romantic retreat in this stunningly large, 1850's remodeled barn apartment. The historic barn is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Sep 20 – 27

G$21,128 GYD per night

Guest favorite

Apartment in Pownal

4.94 out of 5 average rating, 180 reviews

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).

Jun 12 – 19

G$22,721 GYD per night

Guest favorite

Place to stay in Ashfield

5.0 out of 5 average rating, 13 reviews

Norton Hill BnB

Norton Hill BnB is a traditional BnB with a host on site in the heart of scenic Ashfield; The home is spacious and ideal for group and family gatherings. Common areas include the dining room, a parlor, living room, and a porch that overlooks the yard. Please fully review 'The Space' & 'House Rules' details prior to reserving for a party, or a pet.

Jul 12 – 19

G$153,149 GYD per night