Guesthouse vacation rentals in Western Massachusetts
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Western Massachusetts
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Western Massachusetts guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Clarksburg
4.9 out of 5 average rating, 240 reviewsMountain Cottage Spectacular Views
Jul 21 – 28
Guesthouse in Granville
4.9 out of 5 average rating, 785 reviewsMoon Valley Country Retreat no clean fee pets yes
Nov 3 – 10
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Jan 1 – 8
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Sep 26 – Oct 3
Guesthouse in Shrewsbury
4.71 out of 5 average rating, 196 reviewsA Comfy Hilltop Home
Sep 8 – 15
Guesthouse in Charlestown
4.88 out of 5 average rating, 269 reviewsCozy All Season Cabin Near Beach at Rockbriar Farm
Feb 19 – 26
Guesthouse in Springfield
4.86 out of 5 average rating, 321 reviewsConnecticut River-Cozy Cottage
Jan 21 – 28
Guesthouse in Schuylerville
4.97 out of 5 average rating, 380 reviewsGuesthouse in the Country near Saratoga Springs
Oct 31 – Nov 7
Guest house rentals with a patio
Guesthouse in Uxbridge
5.0 out of 5 average rating, 124 reviewsZen Inspired Private Suite with 2-mile Trail Loop
Apr 7 – 14
Guesthouse in Mahopac
4.96 out of 5 average rating, 112 reviewsSunny Lakeview Guesthouse
Dec 21 – 28
Guesthouse in Gardiner
4.99 out of 5 average rating, 137 reviewsRed Barn Retreat - Shawangunk Mountains Getaway
Jun 12 – 19
Guesthouse in Derry
4.96 out of 5 average rating, 111 reviewsThe Carriage House, A Modern Farmhouse
Apr 12 – 19
Guesthouse in Montgomery
4.93 out of 5 average rating, 119 reviewsLuxury mins from angry orchard and city winery
Sep 24 – Oct 1
Guesthouse in Saratoga Springs
4.97 out of 5 average rating, 119 reviewsWake up at the Track on Historic Union Ave!!!
Mar 2 – 9
Guesthouse in Sharon
5.0 out of 5 average rating, 65 reviewsCottage with a Waterfall View
Sep 15 – 22
Guesthouse in Cobleskill
4.93 out of 5 average rating, 69 reviewsupstate caverns b&b
Jul 7 – 14
Guest house rentals with a washer and dryer
Guesthouse in Northampton
4.94 out of 5 average rating, 178 reviewsLittle Blue Studio
Sep 29 – Oct 6
Guesthouse in North Adams
5.0 out of 5 average rating, 208 reviewsNetherwood - North Adams Guest House with Views
Oct 1 – 8
Guesthouse in Glastonbury
4.96 out of 5 average rating, 133 reviewsUnique luxurious private building in historic area
Sep 18 – 25
Guesthouse in Mystic
4.99 out of 5 average rating, 541 reviewsGorgeous Waterfront Getaway
Jan 7 – 12
Guesthouse in Marlboro
4.99 out of 5 average rating, 140 reviewsRefined, serene and like no other, Marlboro, VT.
Oct 20 – 27
Guesthouse in Wallingford
4.98 out of 5 average rating, 589 reviewsVermont Home Central to Ski Areas-No Cleaning Fees
Jan 31 – Feb 7
Guesthouse in Belmont
4.99 out of 5 average rating, 200 reviewsCharming Pool/Garden Guest House
Oct 24 – 31
Guesthouse in Stonington
4.97 out of 5 average rating, 223 reviewsTrue Artist Loft, 5 minutes to downtown Mystic
Aug 4 – 11
Destinations to explore
- Cambridge Vacation rentals
- New Haven Vacation rentals
- Lake George Vacation rentals
- Providence Vacation rentals
- Catskill Vacation rentals
- Albany Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Guesthouse rentals United States
- House rentals United States
- House rentals Boston
- Guesthouse rentals Boston
- House rentals New York
- Guesthouse rentals New York
- House rentals New Hampshire
- Guesthouse rentals New Hampshire
- House rentals Massachusetts
- Guesthouse rentals Massachusetts
- Waterfront rentals Western Massachusetts
- Rentals with a patio Western Massachusetts
- Smoking-friendly rentals Western Massachusetts
- Rentals with an EV charger Western Massachusetts
- Rentals with a sauna Western Massachusetts
- Lakehouse rentals Western Massachusetts
- Pet-friendly rentals Western Massachusetts
- Rentals with a washer and dryer Western Massachusetts
- Farmstay rentals Western Massachusetts
- Chalet rentals Western Massachusetts
- Boutique hotel rentals Western Massachusetts
- Rentals with a home theater Western Massachusetts
- Rentals with a kayak Western Massachusetts
- Condo rentals Western Massachusetts
- Cabin rentals Western Massachusetts
- Hotel rentals Western Massachusetts
- Rentals with breakfast Western Massachusetts
- Wheelchair accessible rentals Western Massachusetts
- Apartment rentals Western Massachusetts
- House rentals Western Massachusetts
- Rentals with a fireplace Western Massachusetts
- Bed and breakfasts Western Massachusetts
- Cottage rentals Western Massachusetts
- Kid-friendly rentals Western Massachusetts
- Rentals with lake access Western Massachusetts
- Beachfront rentals Western Massachusetts
- Monthly Rentals Western Massachusetts
- Fitness-friendly rentals Western Massachusetts
- Ski-in/ski-out rentals Western Massachusetts
- Rentals with outdoor seating Western Massachusetts
- Vacation home rentals Western Massachusetts
- Rentals with an accessible height toilet Western Massachusetts
- Rentals with beach access Western Massachusetts
- Family-friendly rentals Western Massachusetts
- Rentals with a fire pit Western Massachusetts
- Townhouse rentals Western Massachusetts
- Rentals with a hot tub Western Massachusetts
- Private suite rentals Western Massachusetts
- Rentals with pools Western Massachusetts
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes