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Bed and breakfast vacation rentals in Pioneer Valley

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Top-rated bed and breakfast rentals in Pioneer Valley

Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
A sunlit family room features a high wooden ceiling and large windows allowing natural light to flood in. Comfortable seating is provided by a floral-patterned couch and wooden chairs. A wooden coffee table centers the space, complemented by a media unit positioned against the wall.
Private room in Northampton
4.95 out of 5 average rating, 902 reviews

Warm Country Home Minutes from Town

Comfortable, clean, quiet room and private bathroom. We are 10 minutes away from our vibrant downtown. You have access to the living and dining room, patio, yard, and nearby hiking trails. We love hosting and we take our hosting seriously to make our guests happy. Please understand that you are booking a homeshare listing, sharing some spaces with us if you choose to. Although our older home is “lived in," we work hard to make our home clean. We and our lovely cats are hoping to meet you!

ValueFamilyEV charging

Guest favorite
Private room in Suffield
4.92 out of 5 average rating, 114 reviews

The Lily House - Liv's Garden Room

Set in the historic district of Suffield, CT, this charming Victorian home offers a lovely place to stay as you journey through a quaint New England town. It has well appointed rooms, a beautiful wrap-around front porch and several gardens with walking paths. Just a short walk away from fine and casual dining, parks, the “Walk of Homes” as well as Suffield Academy. Our convenient location is only five miles from Bradley Int'l Airport and minutes from both Hartford CT, and Springfield MA.

LocationFamilyShared spaces

Top guest favorite
A bright bedroom features a king bed with a striped blanket and cotton sheets. Two bedside lamps provide warm lighting, and a rocking chair is present beside a small table. A window dressed with sheer curtains allows natural light to enter the room.
Private room in Deerfield
4.99 out of 5 average rating, 192 reviews

King Suite with Breakfast • Near Attractions • 5*

Bright room with king bed, cotton sheets, own bathroom, sleep sofa, and a private porch. We bring a breakfast to your door to start your day right - because it’s not just AirB! Tucked away below Deerfield Ridge: four minutes' drive to Deerfield Academy, Eaglebrook, Bement, and just 17 miles to Amherst or Northampton and their colleges. If you like a secluded spot, you will be happy here with us and we will respect your privacy. The entrance is the only shared space.

LocationFamilyComfort

Guest favorite
Private room in Agawam
4.88 out of 5 average rating, 316 reviews

Hampshire Room

Welcome! Our Hampshire Room is a comfortable private room w/ a brand new king bed, a laptop-friendly workspace, Wi-fi, and 40" flat screen. Conveniently next to bathroom. Convenient access: - MGM Casino-7 min - Bradley Airport-15 min - Eastern States Exposition, home of The Big E-5 min - Basketball Hall of Fame-8 min - Six Flags New England-10 min TWO extremely friendly cats, Tigger & Pounce will greet you and permit oodles of loving.

FamilyLocationAmenities

Top guest favorite
Private room in Brimfield
4.96 out of 5 average rating, 452 reviews

New England Escape

We would love to have you stay at our home. ONLY 5 minutes from Old Sturbridge Village and the Brimfield Antique and Collectibles Show! Also, close to local breweries, tourist attractions, wedding destinations, the airports, and the 3 largest cities in MA. (one hour from both Logan International and Bradley International Airports.) Perfect for couples, singles, or business travelers.

ValueFamilyAmenities

Top guest favorite
The charming stone cottage features a vibrant blue door and flower boxes filled with colorful plants. Lush greenery surrounds the entrance, and original brick walkways lead to the home. Sunlight filters through the trees, creating a welcoming atmosphere outside.
Guesthouse in Granby
4.98 out of 5 average rating, 917 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!

FamilyValueLong stay

Top guest favorite
Private room in Amherst
4.91 out of 5 average rating, 245 reviews

OrchardSlope

"The best of the "feel right at home" AirBnb experiences. Loved it." Former guest of OrchardSlope "The Art of Hosting as an emerging peace practice - the art of caring for." Toke Moeller OrchardSlope is a single family home where we welcome and share with our Airbnb guests. Disclaimer: New photos taken with wide-angle lens are somewhat distorted. Thank you!

ValueFamilyHospitality

Top guest favorite
The exterior features a two-level home with a front porch adorned with seating. A vibrant garden filled with colorful flowers and greenery surrounds the entrance. Decorative elements, such as hanging planters and garden lights, complement the serene landscape.
Apartment in Pownal
4.95 out of 5 average rating, 205 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).

FamilyValueTV

Guest favorite
The entrance of a traditional BnB features a vibrant orange facade and a prominently displayed red door. Two white columns frame the entry, while a charming balcony is visible above. Seasonal flowers in pots add a welcoming touch to the porch area, which is adorned with fallen leaves.
Place to stay in Ashfield
5 out of 5 average rating, 14 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.

FamilyLocationBreakfast

Guest favorite
A cozy living area features two light grey armchairs positioned around a rustic wooden coffee table. Decorative items are arranged on the table, and wood beams add character to the ceiling. A dining area with a black table and chairs is visible in the background.
Cottage in Goshen
4.95 out of 5 average rating, 172 reviews

Stuart Cottage/Minutes to Mohawk Ski Area

The Stuart Cottage is located on the grounds of the Mary Stuart House Bed and Breakfast. Owned by Mary and managed by Elizabeth, the cottage has one bedroom, wifi and plenty of charm...truly the perfect place to relax in a rustic, low-key location in the heart of the Litchfield Hills. Mohawk Mountain and Tyler lake are just a short car ride.

LocationFamilyView

Top guest favorite
A bright hallway extends through the upper level, featuring exposed wood beams and soft yellow walls. Vintage framed artwork is displayed alongside a small table with fresh flowers. A doorway leads to a cozy space lined with bookshelves, inviting quiet reading moments.
Barn in Guilford
4.99 out of 5 average rating, 135 reviews

The Carriage Barn

Situated on a 1792 Vermont farmstead, the original Carriage Barn is a thoughtfully renovated 2-bedroom cottage that blends historic charm with colorful, comfortable design. Located just 10 minutes from Brattleboro and all that Southern Vermont has to offer, it’s a perfect home base for a cozy New England escape.

LocationFamilyWifi

Guest favorite
Private room in Hadley
4.83 out of 5 average rating, 384 reviews

The 1797 House/Locke bedroom along CT River

Welcome to the Captain Locke room in the historic 1797 House (its birth year) in one of America’s oldest English settlements. We now welcome the world to our home along the Connecticut River. Close to UMass, Mount Holyoke, Amherst, Smith and Hampshire colleges, as well as Northampton & I-91.

FamilyLocationOutdoor spaces

Popular amenities for Pioneer Valley bed and breakfast rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly bed and breakfast rentals

Top guest favorite
Private room in Deerfield
4.99 out of 5 average rating, 221 reviews

Queen Suite with Breakfast • Near Attractions • 5*

LocationFamilyTV

A bright bedroom is highlighted by blue walls and soft lighting. A Queen bed is dressed in fresh linens, with colorful pillows offering a touch of comfort. A gas fireplace adds warmth, and a cozy chair is positioned nearby, complementing the serene decor.
Hotel room in Lenox

★ Private Romantic Room with Jacuzzi Tub & Fireplace

LocationIndoor spacesBreakfast

A cozy bedroom features a metal bed frame with crisp white linens and a colorful striped throw. Vintage decor includes a framed pennant and an old political poster. A wall-mounted coat rack provides storage, and soft lighting creates a welcoming ambiance.
Private room in Great Barrington
5 out of 5 average rating, 30 reviews

Granville House - Queen traditional

LocationSleep qualityDecor

The spacious bedroom features a large bed with layered bedding, surrounded by warm, earthy tones. A patterned accent wall complements the room's decor. A mirror reflects the bright natural light coming through the window, while a charming seating area is positioned near the window.
Private room in Sheffield
5 out of 5 average rating, 3 reviews

Ground floor king bedroom in vintage farmhouse BnB

WalkabilityNearbyHospitality

Guest favorite
A small dining area features a round glass table surrounded by two upholstered chairs, adorned with a decorative pattern. A wooden cabinet is visible in the background, complemented by a painting of fruit on the wall. A wine bottle and a menu are displayed on the table.
Private room in West Stockbridge
5 out of 5 average rating, 7 reviews

Standard Suite at Shaker Mill Inn

LocationOutdoor spacesNearby

Top guest favorite
A spacious backyard is featured, showcasing a large in-ground pool surrounded by a paved deck. Loungers and a shaded umbrella provide seating options, while the house's clean white exterior is visible in the background, enhancing the outdoor relaxation area.
Private room in Bennington
4.99 out of 5 average rating, 138 reviews

E and E’s B and B Queen Bed Rm+ Pool & Hot Tub

FamilyLocationHiking

A spacious room features a king-sized sleigh bed with white bedding. Natural light filters in through two bay windows adorned with light drapes. A television is mounted on the wall, and warm lighting is provided by a table lamp and a floor lamp.
Private room in Wilmington
5 out of 5 average rating, 4 reviews

Wilmington Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

LocationHospitalityCleanliness

Guest favorite
A table setting features a plate of French toast topped with banana slices and raspberries, surrounded by a small bowl of whipped cream. A glass of orange juice and a cup of coffee sit nearby, with silverware neatly arranged on a textured place mat.
Private room in Brattleboro
4.92 out of 5 average rating, 107 reviews

The Purple Chef's House single private room

FamilyValueBiking

Bed and breakfast rentals with breakfast

Private room in South Hadley
5 out of 5 average rating, 9 reviews

Daniel Stebbins Inn: Joseph Skinner Room

LocationSleep qualityNearby

Top guest favorite
Private room in Windsor
4.88 out of 5 average rating, 26 reviews

Calling all foodies who seek an amazing breakfast!

ValueLocationSleep quality

Guest favorite
A warm living area is highlighted by a traditional fireplace framed by wooden panels. Two sofas with floral and striped patterns are arranged around a central red area rug, accompanied by a small ottoman. Natural light enters through a window, creating a cozy atmosphere.
Private room in Ashford
5 out of 5 average rating, 10 reviews

Henrietta Suite

LocationCleanlinessAir conditioning

Top guest favorite
Private room in Norfolk
4.98 out of 5 average rating, 54 reviews

Maple House, Birch Room

LocationWalkabilityCheck-in

Top guest favorite
Private room in Amherst
4.93 out of 5 average rating, 215 reviews

BigSkyHilltop: Queen & single bed, full breakfast

LocationValueIndoor spaces

A historic home built in 1797 is showcased with a classic architectural style. The structure features multiple stories, large windows with dark shutters, and decorative bunting. Lush greenery surrounds the exterior, enhancing the inviting presence of the property.
Private room in New Marlborough
5 out of 5 average rating, 15 reviews

The Inn at Freeman Elms Farm B&B- Harriot's Room

LocationNearbyCheck-in

Superhost
A spacious room is furnished with a queen-size bed, two accent chairs, and a wooden dresser. A flat-screen TV is mounted on the wall, and light-colored walls provide a bright atmosphere. The hardwood floor adds warmth to the space.
Private room in Norfolk
5 out of 5 average rating, 4 reviews

C14 Carriage House at Blackberry River Inn

BathroomHikingCleanliness

Superhost
A rustic accommodation features a wooden bed frame with an upholstered headboard. Soft, neutral bedding is complemented by a decorative pillow. A bedside lamp offers warm lighting, and a small table is positioned next to the bed, enhancing the room's cozy feel. A wooden chair and nightstand complete the space.
Private room in Lenox
4.6 out of 5 average rating, 5 reviews

Whistler's Inn/The Santa Fe Room (#12)

LocationWalkabilityQuiet

Bed and breakfast rentals with a patio

Guest favorite
A queen bed features a classic four-poster frame, complemented by soft white linens. Vintage wallpaper with a floral pattern adorns the walls. Soft lighting is provided by sconces on either side of the bed, creating a warm and inviting ambiance.
Private room in Litchfield County
4.94 out of 5 average rating, 17 reviews

Private en-suite Bedroom in Historic Inn

LocationValueSleep quality

A historic inn is illuminated by warm lights along its architectural features, creating a welcoming ambiance against the snowy backdrop. The wraparound porch is adorned with white railings, and windows offer glimpses of the interior glow, highlighting the inviting atmosphere of the retreat.
Private room in Lenox

The Cornell Inn Lenox

The exterior of the Goldenrod Country Inn is depicted, showcasing a classic New England style with a white facade and dark roof. Lush green landscaping and flower beds frame the entrance, while a sign displaying the inn's name stands prominently at the front.
Private room in Worthington

The Audubon Room - Goldenrod Country Inn

A historic house is illuminated by soft lights during a snowy evening. The wraparound porch is decorated, and windows glow warmly. Snow blankets the ground, highlighting the architectural details of the building, while evergreens frame the scene.
Private room in Lenox

The Cornell Inn Lenox

A historic inn is illuminated against a snowy night backdrop, with white string lights outlining its architectural details. The welcoming porch features rocking chairs, while windows emit warm light, suggesting a cozy interior. Snow blankets the surrounding grounds, enhancing the tranquil winter scene.
Private room in Lenox

The Cornell Inn Lenox

A historic inn is presented in the evening, adorned with warm white lights outlining the roof and porch. Snow gently falls around the property, creating a serene winter scene. The large front porch features white railings, with windows glowing from within, inviting guests to relax.
Private room in Lenox

The Cornell Inn Lenox

The exterior of the Goldenrod Country Inn is depicted, showcasing the two-story structure with a welcoming front porch. Lush greenery and colorful landscaping set a serene atmosphere. The inn's signage is visible, highlighting its classic charm in a woodland setting.
Private room in Worthington

The Homestead Room - Goldenrod Country Inn

The exterior of the Goldenrod Country Inn features a classic design with large white siding and dark roof shingles. Lush greenery and blooming flowers surround the entrance, complemented by a welcoming sign. The spacious porch offers seating and views of the landscaped yard.
Private room in Worthington

The Arbor Room - Goldenrod Country Inn

BreakfastShared spaces

Destinations to explore