
Vacation rentals in Tolland
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Tolland
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Tolland vacation rentals
Other great vacation rentals in Tolland
Top guest favorite

Home in Athens
5 out of 5 average rating, 38 reviewsPerfect home for a getaway from NYC
ScottRating, 5 stars1 month ago
Antonio and Yoon's place was perfect for our large group and dog. It's a very spacious home that is thoughtfully designed and in a lovely residential community. The beds and furniture were extremely comfortable, the backyard huge with a large patio and a fire pit. The six bedrooms, three full bathrooms, two living rooms, dining room, fully stocked kitchen, and finished basement gave our group of ten adults more than enough room to both gather together and enjoy time on our own. The location is near wonderful hikes and great restaurants and shops in Athens, Catskill, Hudson, and more. Antonio and Yoon were proactive, friendly, and clear in all communications. Highly recommended!
Top guest favorite

Home in Millerton
4.96 out of 5 average rating, 185 reviewsVacation Home In Millerton
BettyRating, 5 stars2 weeks ago
We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!
Superhost

Home in Litchfield County
4.8 out of 5 average rating, 10 reviewsCharming home ready for fun and/or relaxation!
JadeRating, 5 stars2 months ago
We came to Norfolk for a show at the Infinity Music Hall. This house was a perfect landing spot to cook dinner before and relax after the show. It was so peaceful watching the snow fall from inside and the kitchen was perfectly stocked with everything we needed to cook. The appliances were top notch, the house was well decorated and we will definitely rent here again!
Guest favorite

Home in Monroe
4.93 out of 5 average rating, 14 reviewsThe Camp
BrendaRating, 5 stars3 months ago
We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!
Top guest favorite

Home in Great Barrington
5 out of 5 average rating, 13 reviewsGreat Barrington Ranch. Sleeps 10,Hot Tub, 5 acres
JuanRating, 5 stars1 month ago
We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!
Superhost

Home in Cornwall
4.82 out of 5 average rating, 97 reviewsState Forest Getaway
SahilyRating, 5 stars1 week ago
This Airbnb was a great place to stay at. Although my family didn’t stay long, we just wanted to get out of the routine and find a place to relax for a bit and forget about day to day responsibilities. This place was clean and the host was very friendly; I would 10/10 recommend this place to others!
Top guest favorite

Home in Athens
5 out of 5 average rating, 16 reviewsLake house with arcade games
AdrienneRating, 5 stars3 months ago
Rosane and Daniel's place was great. Very clean and comfortable. It was well stocked with everything we needed.
Guest favorite

Home in Tannersville
4.93 out of 5 average rating, 28 reviewsLuxury Spacious Private Home w/tub! Enjoy Spring
SantiagoRating, 5 stars2 months ago
It’s a fantastic place to stay—a well-designed, private home with a great layout. Conveniently located near the mountain, it’s perfect for skiing while still offering a peaceful retreat.
Destinations to explore
- Hudson Valley Vacation rentals
- The Hamptons Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Pocono Mountains Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Montreal Vacation rentals
- 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
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Six Flags New England
- Berkshire East Mountain Resort
- TPC River Highlands
- Taconic State Park
- Bushnell Park
- Thunder Ridge Ski Area
- Mohawk Mountain Ski Area
- Mount Greylock Ski Club
- Mount Sugarloaf State Reservation
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Sleeping Giant State Park
- Hartford Golf Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Naumkeag
- Beartown State Forest
- Otis Ridge
- Mount Southington Ski Area
- Brownstone Adventure Sports Park
- Rockledge Golf Club
- WIckham Park
- 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