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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Tolland holiday rentals

A rural property with a wooden barn, a white fence, and a mobile home.

1. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is £132
includes taxes & fees
10 Nov - 11 Nov
Cozy Camper tucked into the woods
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

2. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is £215
includes taxes & fees
12 Nov - 13 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A square fire pit with flames, surrounded by a grassy field and a green chair.

3. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (26 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is £134
includes taxes & fees
10 Nov - 11 Nov
Peaceful Meadow Retreat
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

4. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (55 reviews)
"It was a nice stay…worked well for the event we attended in town. The host was very nice to work with"
United States
Roberta S.
The price is £156
includes taxes & fees
22 Nov - 23 Nov
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A house with a porch, a garden with pink flowers, and a stone wall along the road.

5. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (156 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
The price is £262
includes taxes & fees
10 Nov - 11 Nov
Big farmhouse in the foothills of the Berkshires
A hot tub with a string of lights above it, set against a dark night sky.

6. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is £273
includes taxes & fees
10 Nov - 11 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A wooden cabin interior with a bench, a rug, and a hanging plant.

7. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (5 reviews)
The price is £144
includes taxes & fees
15 Nov - 16 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

8. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is £270
includes taxes & fees
10 Nov - 11 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

9. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is £88
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern kitchen with blue cabinets, a central island, and a dining area with a glass table and chairs.

10. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
9.6 out of 10, Exceptional, (4 reviews)
"Cute and cozy home away from home! We loved our stay and all the nice features there were!! Everything was neat and clean and host was super amazing and helpful! We definitely will choose this place again if we’re ever in the area."
United States
Leah H.
The price is £104
includes taxes & fees
11 Nov - 12 Nov
Collinsville River Escape / Fall Foliage, Deck & Yard
A reception area with a counter, a plant, and an exit sign.

11. 1 Queen Bed | Micfridge

1 Queen Bed | Micfridge
Windsor Locks
10.0 out of 10, Exceptional, (51 reviews)
"Near the airport, this place made for a quick and easy stay."
United States
Anonymous traveller
The price is £67
includes taxes & fees
10 Nov - 11 Nov
1 Queen Bed | Micfridge
A two-story house with a front porch, a small balcony, and a white picket fence.

12. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
The price is £268
includes taxes & fees
10 Nov - 11 Nov
Cozy Attic 10 min to Llitchfield
A balcony with a view of a lake, white railings, and outdoor furniture.

13. River Overlook - What a view from your deck!

River Overlook - What a view from your deck!
Collinsville
10.0 out of 10, Exceptional, (27 reviews)
"I only did a short stay (2 nights) but it was super adorable! I will definitely stay again when I'm back in the area."
United States
Mary S.
The price is £228
includes taxes & fees
10 Nov - 11 Nov
River Overlook - What a view from your deck!
A reception area with a counter, a plant, and an exit sign.

14. 1 Queen Bed | ADA/Tub/Micfridge

1 Queen Bed | ADA/Tub/Micfridge
Windsor Locks
10.0 out of 10, Exceptional, (53 reviews)
"The pool area was clean and relaxing, perfect for unwinding after a busy day."
United States
Anonymous traveller
The price is £67
includes taxes & fees
11 Nov - 12 Nov
1 Queen Bed | ADA/Tub/Micfridge
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

15. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (4 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is £184
includes taxes & fees
16 Nov - 17 Nov
Sun Filled Lake House Living
A cozy room with two beds, large windows, and a view of a snowy landscape.

16. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (79 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is £196
includes taxes & fees
18 Nov - 19 Nov
The Creation Station is a cozy place so make yourself at home.
A modern kitchen with stainless steel appliances, a wooden dining table, and a ceiling fan.

17. Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
West Springfield
10.0 out of 10, Exceptional, (1 review)
"Adorable home, set up so cute plus being pet friendly means everything to me when deciding. All was as described and our host had everything you could need and more available to us in the well stocked kitchen and bathroom. Very quiet safe and friendly neighborhood on a dead end street, gated walkway as well as a gated driveway made me feel plenty safe enough to take my dog out at night. Bedrooms were welcoming and set up with pretty fairy lights throughout, all three beds were very comfortable...
United States
Jaimie F.
The price is £237
includes taxes & fees
10 Nov - 11 Nov
Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags
A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

18. Cozy 2-bedroom apartment with movie theater.

Cozy 2-bedroom apartment with movie theater.
Agawam
8.8 out of 10, Excellent, (3 reviews)
"N/A"
United States
Eric R.
The price is £210
includes taxes & fees
10 Nov - 11 Nov
Cozy 2-bedroom apartment with movie theater.
A two-story house with a front porch, a small balcony, and a white picket fence.

19. Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is £308
includes taxes & fees
10 Nov - 11 Nov
Cozy Modern Farmhouse Private Apt - 3 Beds
A residential garden with a stone border, various plants, and a house in the background.

20. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is £225
includes taxes & fees
10 Nov - 11 Nov
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

10/10 Excellent
"Excellent location and conditions. Shuttle airport included is a great option. 2 suggestions: 1) is to training the front desk personnel to receive happy all guests. 2) include the Windsor locks train station in the Hotel shuttle transportation."
Kareen 1-night trip
Posted less than an hour ago
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Find out more about Tolland

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, apart-hotels, 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 favorite 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 depends 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 £88 per night. Entering your travel dates in the search wizard you might find 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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Tolland is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Tolland?

With 6 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. Maple Corner Farm Cross Country Ski Area and Hartland Recreation Area 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.