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Bed and breakfast holiday 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 favourite
A well-lit bedroom features a queen bed dressed in striped linens. Natural light filters through sheer curtains over two windows. A small desk and chair are situated against one wall, while lamps provide additional lighting beside the bed and on a side table. An air conditioning unit is visible.
Private room in Northampton
4.95 out of 5 average rating, 913 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!

FamilyValueLayout

Top guest favourite
A welcoming two-story house is presented in warm red siding, framed by lush green landscaping and mature trees. The front entrance features steps leading up to a covered porch with large windows that allow natural light to flow into the home.
Private room in Pittsfield
4.98 out of 5 average rating, 464 reviews

Large guest suite w/private bath in the Berkshires

A wonderful welcoming house in a beautiful residential neighborhood with no occupancy taxes! We are 15-25 minutes from Tanglewood, Kripalu, Mt Greylock, the Rockwell Museum, MassMoCA, skiing and hiking. Our home is centrally located to all of the fun things to do in the Berkshires. We've lived here for over 20 years and are happy to provide helpful insights for your stay. One of the reasons we love the Berkshires is that each season offers wonderfully unique experiences for any visitor.

FamilyValueLong stay

Guest favourite
An aerial view of a charming Victorian home with a yellow exterior, situated in a lush garden setting. The property features multiple sections, a wrap-around porch, and several landscaped areas with trees and flower beds, creating a welcoming outdoor space.
Private room in Suffield
4.9 out of 5 average rating, 116 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.

ValueLocationCheckout

Top guest favourite
Private room in Deerfield
4.99 out of 5 average rating, 227 reviews

Breakfast Served to your Queen Suite • 5*

Bright room, 2nd floor queen bed, cotton sheets, own bathroom, sitting area, sleep sofa, and deck. We bring a breakfast to your door to start your day right - because it’s not just AirB! Private and close to where you want to be: four minutes' drive to Deerfield Academy, Eaglebrook or Bement, 17 miles to Northampton and Amherst 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.

FamilyValueView

Top guest favourite
A comfortable bedroom features a spacious bed adorned with decorative pillows. Soft blue walls create a calming atmosphere, while two bedside lamps provide warm lighting. A window dressed with light curtains is situated above the headboard, allowing natural light to filter into the room.
Private room in Agawam
4.89 out of 5 average rating, 322 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.

ValueLocationQuiet

Top guest favourite
A historic Victorian home showcases a multi-faceted roof with a prominent turret, featuring vibrant blue siding and decorative trim. Lush greenery and landscaped gardens frame the entrance, which is highlighted by flanking flower pots. The inviting facade is complemented by large, colorful windows.
Private room in Belchertown
5.0 out of 5 average rating, 257 reviews

The Lacey Rose - A Victorian Suite

Large private bedroom and full bath in lovely Victorian home located in the Historic District of Belchertown. Step back in time in this period home decorated with antiques and enjoy the convenience of being near the Five College Area and all that it offers. There are two other rooms available at The Lacey Rose. This beautiful home was built in 1810 as a colonial and renovated into a victorian in the late 1880's.

LocationFamilyHeating

Top guest favourite
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.
Guest house in Granby
4.98 out of 5 average rating, 925 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!

ValueLocationGetting around

Top guest favourite
A welcoming sign made of chalkboard displays the text 'Welcome to OrchardSlope'. It is complemented by decorative items, including a candle within a terracotta holder, small potted succulents in various colors, and additional earthy objects, all arranged on a colorful wooden surface.
Private room in Amherst
4.92 out of 5 average rating, 250 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!

LocationFamilyCleanliness

Top guest favourite
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.
Flat in Pownal
4.95 out of 5 average rating, 206 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).

FamilyValueHeating

Guest favourite
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
5.0 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.

LocationFamilyIndoor spaces

Guest favourite
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
4.94 out of 5 average rating, 174 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.

FamilyLocationOutdoor spaces

Top guest favourite
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, 136 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.

LocationFamilyNearby

Popular amenities for bed & breakfast rentals in Pioneer Valley

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly bed & breakfast rentals

Superhost
The spacious room features a queen bed with decorative bedding and a sleep sofa. A seating area is included with a coffee table and soft armchairs. Natural light floods through large windows, and the private bath is accessible through an adjacent door.
Private room in West Stockbridge
4.67 out of 5 average rating, 3 reviews

Superior Suite with a Patio Pets allowed

LocationCleanlinessComfort

A four-poster canopy bed with decorative lace draping is centered in the room, layered with soft white and red bedding. A rich rug covers the oak floor, complemented by floral curtains framing two windows. A seating area features a plush wing chair and a wooden dresser.
Private room in Stockbridge
4.75 out of 5 average rating, 4 reviews

Stockbridge #1 B&B Full Breakfast Close to Museums

LocationBreakfastDecor

A spacious suite features a king-sized bed with crisp white linens and a decorative throw. Soft glowing lights highlight framed artwork on the wall. A separate seating area includes a comfortable couch, with a window overlooking the outdoors, creating an inviting atmosphere.
Private room in Great Barrington
5.0 out of 5 average rating, 12 reviews

Granville House - King Suite

LocationComfortBathroom

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
5.0 out of 5 average rating, 4 reviews

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

LocationComfortWalkability

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
5.0 out of 5 average rating, 3 reviews

Ground floor king bedroom in vintage farmhouse BnB

HospitalityBreakfastWalkability

Guest favourite
The exterior of a charming two-story building is surrounded by vibrant flower beds filled with yellow and orange blooms. A flagpole stands prominently, displaying the American flag. The building features a pitched roof and stairs leading to a second-level entrance.
Private room in Halifax
4.97 out of 5 average rating, 31 reviews

Baked Apples at Shearer Hill Farm B&B Room 1

ValueFamilyComfort

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 spacesCheck-in

Top guest favourite
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, 200 reviews

Breakfast Served to your King Suite • 5*

FamilyLocationOutdoor spaces

Bed and breakfast rentals with breakfast

Top guest favourite
Private room in Brimfield
4.96 out of 5 average rating, 462 reviews

New England Escape

LocationFamilySolo travel

Top guest favourite
A well-lit bedroom features two beds: a spacious queen-size bed and a single bed, each adorned with neutral bedding. Natural light flows through multiple windows, complemented by wooden furnishings and a bedside lamp. A framed artwork adds a personal touch to the inviting atmosphere.
Private room in Amherst
4.93 out of 5 average rating, 216 reviews

BigSkyHilltop: Queen & single bed, full breakfast

FamilyValueComfort

Top guest favourite
A cozy living room is characterized by wooden beams and warm wood paneling. Comfortable seating is arranged around a central area rug, with plants adorning the space. Natural light fills the room through large sliding glass doors that open to a deck.
Private room in Sandisfield
4.94 out of 5 average rating, 160 reviews

Hospitality in the Berkshire Woods

FamilyLocationCheck-in

Top guest favourite
A well-appointed bedroom features a spacious bed with a light blue quilt and decorative pillows. An elegant fireplace is positioned against the wall, complemented by a framed floral artwork. Soft natural light pours in through sheer curtains, enhancing the calming atmosphere.
Private room in Norfolk
4.98 out of 5 average rating, 56 reviews

Maple House, Birch Room

FamilyLocationHospitality

Superhost
A cozy guest room features a spacious bed with a floral quilt. A comfortable chair sits in the corner beside a window adorned with curtains. Wooden beams highlight the ceiling, and a decorative area rug covers the hardwood floor. A coat rack adds to the room's simplicity.
Private room in Rowe
5.0 out of 5 average rating, 5 reviews

Maple House B&B - Room #2 - View of Yesteryear

FamilyLocationNearby

Guest favourite
A cozy sleeping area features a floral-patterned quilt and matching pillows on a spacious bed. Soft light falls on the bed from a nearby lamp, illuminating the green walls. Artwork hangs above the bed, and a small wooden nightstand sits beside it.
Private room in Lenox
4.88 out of 5 average rating, 34 reviews

Whistler's Inn/The Petite Chambre (#11)

LocationFamilyCheckout

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
5.0 out of 5 average rating, 4 reviews

C14 Carriage House at Blackberry River Inn

HospitalityIndoor spacesSleep quality

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

Calling all foodies who seek an amazing breakfast!

ValueLocationGetting around

Bed and breakfast rentals with a patio

Guest favourite
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, 18 reviews

Private en-suite Bedroom in Historic Inn

LocationValueDecor

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

Shared spacesBreakfast

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

Top guest favourite
The exterior of a Victorian home is displayed, featuring a turret and multi-colored shingles. The manicured lawn is bordered by green foliage and decorated with planters. Steps lead to a welcoming entrance, framed by large windows that reflect the surrounding greenery.
Private room in Belchertown
4.98 out of 5 average rating, 131 reviews

The Lacey Rose - The Golden Room

LocationFamilyHot tub

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

A charming New England inn is captured under a gentle snowfall, featuring a white-balustraded balcony illuminated by warm lights. A vintage lamp post stands in the foreground, casting a soft glow amidst the serene winter landscape. Snow-covered branches add a touch of tranquility to the scene.
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 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

Destinations to explore