Tolland Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Tolland

Terrace/patio
Beautiful Home w/ Hot Tub in a Private Lake Community

Vacation Home in Tolland

10.0 out of 10, Exceptional, (3)
"We hope to come back here. The home is clean and its very spacious. The best part is the lake and surrounding area!"
United States
Eli L.
Beautiful Home w/ Hot Tub in a Private Lake Community
Exterior
Beautiful retreat in a lake community to the enjoy the summer season.

Vacation Home in Tolland

10.0 out of 10, Exceptional, (44)
"Property was great!"
United States
Tara G.
Beautiful retreat in a lake community to the enjoy the summer season.
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (136)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow
Game room
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (6)
The price is ￥31,454
￥46,238 total
includes taxes & fees
Dec 8 - Dec 9
Pet Friendly Riverfront Home in Great Barrington
Interior
Peace and quiet on the lake

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake
Fridge, microwave, oven, stovetop
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Apartment in Great Barrington

9.6 out of 10, Exceptional, (38)
"The apartment has everything you might need for a comfortable stay. Perfect location. The host is very responsive and always ready to help. The place is very clean and beautiful. I highly recommend it and will be happy to come back next year. "
United States
Elena
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Dining
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Cabin in Northwest Harwinton

8.6 out of 10, Excellent, (27)
"Love the place.. very clean ..loved the neighbors.. got to catch up on well needed rest.. the neighbors on the right were wonderful than the owners came and they were also wonderful also"
United States
Andrea m.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

Villa in Lenox

10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Vacation Home in Lee

8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is ￥66,015
￥123,882 total
includes taxes & fees
Dec 14 - Dec 15
Spacious 5-bedroom house in charming Lee with WiFi
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Vacation Home in Stockbridge

10.0 out of 10, Exceptional, (135)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Interior
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (53)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,647
￥58,437 total
includes taxes & fees
Dec 8 - Dec 9
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

Vacation Home in Lenox

9.2 out of 10, Wonderful, (33)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is ￥24,884
￥60,935 total
includes taxes & fees
Dec 15 - Dec 16
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Exterior
Antique Farmhouse Totally Restored

Vacation Home in Sheffield

9.8 out of 10, Exceptional, (94)
"The property was beautiful. Very spacious, inside and out. "
United States
Michelle C.
Antique Farmhouse Totally Restored
Exterior
The Blue Elm - A Historic Berkshire Cottage

Cottage in Sheffield

10.0 out of 10, Exceptional, (15)
"It was wonderful!! The hosts were fantastic and the place was lovely. Highly recommend. "
United States
noel s.
The Blue Elm - A Historic Berkshire Cottage
Property grounds
The Creation Station is a cozy place so make yourself at home.

Vacation Home in Easthampton Ma.

10.0 out of 10, Exceptional, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is ￥27,959
￥43,029 total
includes taxes & fees
Dec 8 - Dec 9
The Creation Station is a cozy place so make yourself at home.
Fridge, microwave, oven, stovetop
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Vacation Home in Collinsville

10.0 out of 10, Exceptional, (61)
"A very nice period home in a beautiful setting. The home is immaculate with all of the necessary essentials for an extended stay. The host is very responsive and keeps in touch to ensure that your stay is as enjoyable and comfortable as possible. "
United States
Virginia M.
The price is ￥40,401
￥70,577 total
includes taxes & fees
Dec 8 - Dec 9
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Apartment in Lee

9.4 out of 10, Exceptional, (71)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
United States
Sue P.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Tolland Hotel Reviews

Homewood Suites by Hilton Windsor Locks Hartford

Homewood Suites by Hilton Windsor Locks Hartford

10/10 Excellent
"It was great!"
Dominic 1-night trip
Posted 3 days ago
Homewood Suites by Hilton Windsor Locks Hartford

Find out more about Tolland

Search for holiday rentals in Tolland on Expedia! You can easily find your home rentals, villas, holiday apartments in Tolland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Tolland!

Frequently asked questions

Are there vacation rentals in Tolland?

Yes, you can find vacation rentals close to top local attractions in Tolland, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Tolland has to offer?

Pet Friendly Riverfront Home in Great Barrington: This vacation home rental outside of Tolland is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Tolland?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Tolland stay.

What’s there to see and do in Tolland?

While exploring the area, visit family-friendly sights like Flamig Farm, or get outside and enjoy nature at Otis Reservoir. Maple Corner Farm Cross Country Ski Area and Tolland State Forest are a couple of places you'll find in the larger area.

What’s a vacation rental in Tolland like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Tolland. Vacation rentals offer extras like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for families.