Guesthouse vacation rentals in Windsor County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Windsor County
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 Windsor County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Randolph
4.96 out of 5 average rating, 232 reviewsMacintosh Hill Farm
Guesthouse in Hanover
4.96 out of 5 average rating, 49 reviewsPrivate guest-room 1 mile from Dartmouth
Guesthouse in Strafford
4.93 out of 5 average rating, 137 reviewsSpacious Country Guesthouse
Guesthouse in Springfield
4.86 out of 5 average rating, 323 reviewsConnecticut River-Cozy Cottage
Guesthouse in Woodstock
4.98 out of 5 average rating, 209 reviewsCozy Little Spot (Self Check-in)
Guesthouse in Norwich
4.93 out of 5 average rating, 171 reviewsVermont Log Guest Home-Close to Dartmouth
Guesthouse in Hartland
4.95 out of 5 average rating, 914 reviewsYurt In The Woods - Private Refuge
Guest house rentals with a patio
Guesthouse in Chester
5.0 out of 5 average rating, 13 reviewsThe Lodge
Guesthouse in Chester
5.0 out of 5 average rating, 13 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
Guesthouse in Mount Holly
4.96 out of 5 average rating, 54 reviewsMoon Acre Farm Green Mountain Oasis - near Okemo
Guesthouse in Lebanon
4.96 out of 5 average rating, 48 reviewsPrivate guesthouse in Lebanon
Guesthouse in Hartford
4.93 out of 5 average rating, 42 reviewsAddie's Place
Guesthouse in Reading
5.0 out of 5 average rating, 11 reviewsPeace & quiet at Comet Farm
Guest house rentals with a washer and dryer
Guesthouse in Plymouth
4.97 out of 5 average rating, 97 reviewsQuiet Vermont Retreat near Killington and Okemo
Guesthouse in Andover
4.88 out of 5 average rating, 104 reviewsQuiet Self Contained Apartment in Vermont Hills
Guesthouse in Ludlow
5.0 out of 5 average rating, 3 reviewsThe Black Sheep Barn
Guesthouse in Killington
4.6 out of 5 average rating, 5 reviewsThe Apartment at the Slopeside Estate House!
Guesthouse in Weston
4.18 out of 5 average rating, 11 reviews1BR dog-friendly mtn cabin with fireplaces
Destinations to explore
- Guesthouse rentals United States
- House rentals United States
- House rentals Vermont
- Guesthouse rentals Vermont
- House rentals Vermont
- Guesthouse rentals Vermont
- Guesthouse rentals New York
- House rentals New York
- Guesthouse rentals New Hampshire
- House rentals New Hampshire
- Waterfront rentals Windsor County
- Rentals with an accessible height toilet Windsor County
- Rentals with a fireplace Windsor County
- Monthly Rentals Windsor County
- Rentals with breakfast Windsor County
- Beachfront rentals Windsor County
- Bed and breakfasts Windsor County
- Rentals with lake access Windsor County
- Villa rentals Windsor County
- Rentals with a patio Windsor County
- Rentals with outdoor seating Windsor County
- Farmstay rentals Windsor County
- Tiny house rentals Windsor County
- Ski-in/ski-out rentals Windsor County
- Rentals with a washer and dryer Windsor County
- Rentals with a kayak Windsor County
- Kid-friendly rentals Windsor County
- Cabin rentals Windsor County
- Chalet rentals Windsor County
- Condo rentals Windsor County
- Rentals with a fire pit Windsor County
- Townhouse rentals Windsor County
- House rentals Windsor County
- Private suite rentals Windsor County
- Rentals with an accessible height bed Windsor County
- Rentals with a sauna Windsor County
- Apartment rentals Windsor County
- Fitness-friendly rentals Windsor County
- Cottage rentals Windsor County
- Rentals with pools Windsor County
- Rentals with an EV charger Windsor County
- Pet-friendly rentals Windsor County
- Rentals with a hot tub Windsor County
- Rentals with beach access Windsor County
- Family-friendly rentals Windsor County
- 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