
Bed and breakfast holiday rentals in Western Massachusetts
Find and book unique bed and breakfasts on Airbnb
Top-rated bed and breakfasts in Western Massachusetts
Guests agree: These bed and breakfast rentals are highly rated for location, cleanliness and more.

Palazzo Hudson: Luxury Home w/Pool, Hot tub, Sauna
Welcome to Palazzo Hudson! The only private vacation home in Hudson proper with a deluxe sauna, cedar hot tub, seasonal in-ground pool, chef's kitchen, & a pool-side lounge with a fireplace & art library! A home for all seasons, you'll experience inspiration and relaxation from the warm, light-filled rooms, curated art, books, music, luxury spa features, and outdoor deck, patios, and gardens. A quick stroll to the restaurants, bars, cafes, and shops of Warren Street & the Upper Depot District.

Ridge with a View 1000 sf private guest suite/pool
Private, 3 story home w/forest view of President Grants Cottage on Mt. McGregor. Exclusive walkout basement w/ pool outside your door. Living area (800sf), private bedroom (200sf), & full bath. Microwave/mini fridge/coffee (no kitchen sink/cooking). Own parking spot (must walk through the grass to get to your entrance). Breakfast menu offered 7-10am each morning. Homemade cookies upon arrival. 8 miles to downtown Toga, 11 to Track, 14 to SPAC, 6 to Adirondack Park & 20 to Lake George

Bucolic Farm On A Country Road
Lovely private 1 bedroom apartment with shared entry. Located in bucolic Lyme Ct. which has nearby beaches, tourist attractions, nature parks, small town living, hiking etc. Sparkling clean! Fully equipped kitchen, dining and living spaces incl laundry. Enjoy the outdoor sitting area with sounds of nature and wildlife. Comfortable furnishings, include a sleeper sofa for an extra guest or 2! Private and peaceful yet close to shopping, dining, area attractions and nature pursuits.

Luxury Cottage on the Potowomut River 2bd/2b
The Cottage at The Grange is located on the peaceful Potowomut River. It is a beautiful and newly renovated 2 bedroom (king, 2 twin beds) / 2 full bath home with all the modern amenities and conveniences expected from a luxury short-term rental while maintaining the historic charm of this colonial estate. Cook a gourmet meal in the stocked kitchen or BBQ on the deck. Situated on 11 pristine acres enjoy private tennis/pickleball courts, kayak access to Greenwich Bay and much more!

~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. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Welcome to the "Red Bridge Cottage"
Welcome to "The Red Bridge Cottage" a 2 minute walk to the Kinderhook Creek (a Hudson River estuary) with the best trout fishing! This newly renovated cottage has all new kitchen appliances including a new washer and dryer. Comforts include: Central AC & whirlpool tub! Locally and only 3 miles away is the Empire State Bike Trail - a 750 mile trail connecting urban centers, village main streets and rural communities with informational boards on the interesting local wildlife.

HotTub FirePit Games Huge Backyard Family Friendly
The ultimate experience for couples & families 5-10min from hiking trails & ski resorts A Mile from Gregg Lake Beach ALL YEAR PRIVATE/SECLUDED HOT TUB Grill, Hammock, Gym equipment XBox Series S, Life Size Janga, Yahtzee, Darts, Corn Hole, ping pong table, mini pool table Luxury KING PURPLE Brand Mattresses in every bedroom for the best nights rest with individual mini splits for optimal comfort Fully stocked kitchen High speed WiFi, house on 2 private acres

Private Suite with Hot Tub
#BarnQuiltHouse Cozy, private guest suite with hot tub in the wooded hills of a quaint New Hampshire farming town. Residential neighborhood, centrally located in Southern New Hampshire. 20+/-min to Concord, Manchester Airport, St. Anselms College, New England College, Pat's Peak, Crotched Mountain. Head north to the lakes region, west to Mt. Sunapee, or south to visit Boston..all within an hour+ drive. May the peace of the wilderness be with you.

Serene Suite: Hudson & Berkshires, Walk to Brewery
A peaceful, highly rated private suite in the heart of historic Hillsdale, where the Hudson Valley meets the Berkshires. Walk to shops, restaurants, a brewery, cooking school, grocery, wine and liquor store. Minutes to Hilltown, the Harlem Valley Rail Trail, scenic hikes, and beautiful drives, with galleries, antiques, live music, and cultural gems nearby. A serene, perfectly located home base for spring dining, exploring, and unwinding.

Hiking Hideaway on the Ridge
Come and enjoy a few days in the Hudson Valley. Located on 7 acres in Beacon, NY, our place is a short ride to Main Street and family-friendly activities including art galleries, restaurants, museums, hiking and sightseeing. The nightlife is lively especially on Second Saturday, and you are only little over an hour by train to NYC. You'll love the secluded ridge location, and your friendly host and hostess.

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!

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).
Popular amenities for Western Massachusetts bed and breakfasts
Family-Friendly Bed and Breakfasts

The Cambridge Retreat House LLC

Best Location Historic College Hill

Johnston Room at The O'Connell House Inn

Private suite in James Colt townhouse

Twin beds in classic New England home near the sea

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

Brick Row House in the Woods, private 2nd floor

Lovely bedroom in Amherst with double bed.
Bed and breakfast rentals with breakfast

Historic House Bed & Breakfast w/art RM #1

OrchardSlope

The Sara Tracy House, Whitman Room

Eva Blake House-Margaret's Room

BigSkyHilltop: Queen & single bed, full breakfast

Next to Skidmore and near Racetrack: Twin Room

Luxury Camping in a Cozy Guest Cottage

Christine's Guest Room near Adirondacks, Saratoga
Bed and breakfast rentals with a patio

Gunks EcoLodge Main Lodge, 3 Bedrooms and 3 Baths

LOCUSTWOOD - ROSÉ ROOM

Farm at Williams River House - Essex Suite

Inglenook Suite | King Bed 1st Floor Vineyard View

Peaceful Room w/ Work Space

Purple Chef's Cozy Apartment

Queen bed + private bath, breakfast included

Spacious King Suite with Fireplace | Lake George
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Fitness-friendly rentals Western Massachusetts
- Cottage rentals Western Massachusetts
- Boutique hotels Western Massachusetts
- Aparthotel rentals Western Massachusetts
- Rentals with breakfast Western Massachusetts
- Ski-in/ski-out rentals Western Massachusetts
- Apartment rentals Western Massachusetts
- Cabin rentals Western Massachusetts
- Beachfront rentals Western Massachusetts
- Smoking-friendly rentals Western Massachusetts
- Tiny house rentals Western Massachusetts
- Rentals with outdoor seating Western Massachusetts
- Townhouse rentals Western Massachusetts
- Chalet rentals Western Massachusetts
- Hotel rooms Western Massachusetts
- Luxury rentals Western Massachusetts
- Farmstay rentals Western Massachusetts
- Condo rentals Western Massachusetts
- Lakehouse rentals Western Massachusetts
- Rentals with pools Western Massachusetts
- Rentals with a kayak Western Massachusetts
- Rentals with beach access Western Massachusetts
- Waterfront rentals Western Massachusetts
- Rentals with a fire pit Western Massachusetts
- Loft rentals Western Massachusetts
- Guesthouse rentals Western Massachusetts
- Rentals with an accessible height toilet Western Massachusetts
- Rentals with a washing machine and dryer Western Massachusetts
- Rentals with a sauna Western Massachusetts
- Rentals with a patio Western Massachusetts
- Family-friendly rentals Western Massachusetts
- Rentals with an EV charger Western Massachusetts
- Rentals with lake access Western Massachusetts
- Private suite rentals Western Massachusetts
- Rentals with a fireplace Western Massachusetts
- Rentals with a home theatre Western Massachusetts
- Pet-friendly rentals Western Massachusetts
- Rentals with a hot tub Western Massachusetts
- House rentals Western Massachusetts
- Holiday home rentals Western Massachusetts
- Bed and breakfasts Massachusetts
- Bed and breakfasts United States
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Mount Snow Ski Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Taconic State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- June Farms
- Ski Sundown
- University of Connecticut
- Naumkeag
- Norman Rockwell Museum
- Hudson Chatham Winery
- Berkshire Botanical Garden
- New York State Museum
- Hancock Shaker Village
- Rensselaer Polytechnic Institute
- Smith College
- The Egg
- University of Massachusetts Amherst
- Things to do Western Massachusetts
- Things to do Massachusetts
- Art and culture Massachusetts
- Food and drink Massachusetts
- Tours Massachusetts
- Sports activities Massachusetts
- Sightseeing Massachusetts
- Nature and outdoors Massachusetts
- Things to do United States
- Sightseeing United States
- Nature and outdoors United States
- Food and drink United States
- Tours United States
- Art and culture United States
- Sports activities United States
- Wellness United States
- Entertainment United States





