Tolland Holiday Rentals

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Holiday Rentals in Tolland

Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, 31 reviews
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat to the woods to enjoy the winter season.
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
9.4 out of 10, Exceptional, 6 reviews
"Cute cabin in a beautiful private setting. Very peaceful and surrounded by nature."
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
10.0 out of 10, Exceptional, 2 reviews
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
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Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, 32 reviews
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, 7 reviews
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, 52 reviews
"Wonderful place to stay, had a great time lots of instruments to try, had lots of space to spread out and hangout, the hot tub was very nice and clean. Overall had a fantastic stay the lighted walkway is amazing! All the amenities available where also great, Jon was a great host and we had a great time speaking with him!"
The price is AU$365
includes taxes & fees
4 June - 5 June
The Creation Station is a cozy place so make yourself at home.
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, 29 reviews
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, 195 reviews
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Peace and quiet on the lake
9.6 out of 10, Exceptional, 184 reviews
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, 3 reviews
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, 3 reviews
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, 49 reviews
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is AU$413
includes taxes & fees
24 June - 25 June
Perfect Vacation Get Away - Historical New Marlborough
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, 6 reviews
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, 2 reviews
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, 4 reviews
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, 7 reviews
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, 12 reviews
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
10.0 out of 10, Exceptional, 56 reviews
"The place was nice and is clean. I knew it was a downstairs of a house. The owner does have a dog that barks from time to time in the evening and you can hear people above, but was not too much to handle. Overall was a nice place in a nice town."
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, 20 reviews
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, 4 reviews
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
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See all available properties in Tolland
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.

Tolland Holiday Home Travel Info

Other types of properties in Tolland you may be interested in

Quality Inn West Springfield
2.5 star property
7.2 out of 10, Good, 1,005 reviews
"Great. Enjoyed the short stay and will come again when I have to"
The price is AU$137
includes taxes & fees
23 June - 24 June
Quality Inn West Springfield
DoubleTree by Hilton Hartford - Bradley Airport
4.0 star property
8.0 out of 10, Very good, 1,002 reviews
"The front desk staff did a great job with check in despite having their computer system down. Air conditioning in the room and restaurant/bar was not as cool as it should have been. "
The price is AU$248
includes taxes & fees
1 July - 2 July
DoubleTree by Hilton Hartford - Bradley Airport
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
2.5 star property
6.4 out of 10, 1,263 reviews
"Quiet and well organized "
The price is AU$131
includes taxes & fees
10 June - 11 June
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
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.

Everything you need to know about Tolland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Tolland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Tolland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Tolland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Tolland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Tolland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Tolland holiday rentals we have selected for you start as low as AU$365 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Tolland rentals

At Expedia, we put the best Tolland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Tolland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Tolland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Tolland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Tolland?

Yes, there are holiday rentals close to the most popular sights in Tolland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Tolland has to offer?

Pristine Home In Becket Woods: This holiday home rental outside of Tolland is located near skiing, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, 1 hot tub and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Tolland?

With 5 Expedia holiday rentals, you're guaranteed 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. Infinity Music Hall and Bistro and Highland Lake are a couple of places you'll find in the wider area.

What’s a holiday rental in Tolland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Tolland. Holiday rentals offer extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips or small group gatherings.

Recent reviews of Tolland properties
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