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Tolland Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Tolland holiday rentals

A square fire pit with flames, surrounded by a grassy field and a green chair.

1. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is NZ$313
includes taxes & fees
10 Sept - 11 Sept
Peaceful Meadow Retreat
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

2. 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, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is NZ$401
includes taxes & fees
1 Sept - 2 Sept
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"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 NZ$472
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
A house with a porch, a garden with pink flowers, and a stone wall along the road.

4. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (149 reviews)
"Great location"
United States
Will G.
The price is NZ$584
includes taxes & fees
3 Sept - 4 Sept
Big farmhouse in the foothills of the Berkshires

5. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
The price is NZ$364
includes taxes & fees
30 Sept - 1 Oct
Cozy Camper tucked into the woods
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
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is NZ$663
includes taxes & fees
7 Sept - 8 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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.

7. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$619
includes taxes & fees
9 Sept - 10 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is NZ$279
includes taxes & fees
7 Sept - 8 Sept
Cozy 1-bedroom studio in serene Great Barrington with AC

9. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is NZ$564
includes taxes & fees
7 Sept - 8 Sept
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
A spacious kitchen with a large island, wooden beams, and pendant lighting.

10. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is NZ$630
includes taxes & fees
13 Sept - 14 Sept
Linny's - Private Dock - Lake Access - Firepit
A loft bedroom with a television, wooden shelves, a ladder, and a skylight.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is NZ$376
includes taxes & fees
1 Sept - 2 Sept
Peaceful and cozy 1 bed 1 bath in quaint Winchester
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
9.4 out of 10, Exceptional, (6 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 NZ$570
includes taxes & fees
1 Sept - 2 Sept
Cozy Attic 10 min to Llitchfield
A cozy room with two beds, large windows, and a view of a snowy landscape.

13. 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, (77 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 NZ$463
includes taxes & fees
14 Sept - 15 Sept
The Creation Station is a cozy place so make yourself at home.
A two-story house with a front porch, a small balcony, and a white picket fence.

14. 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 NZ$690
includes taxes & fees
1 Sept - 2 Sept
Cozy Modern Farmhouse Private Apt - 3 Beds
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

15. Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is NZ$727
includes taxes & fees
1 Sept - 2 Sept
Art House 3 Beds Close to Warner Theater
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

16. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
The price is NZ$460
includes taxes & fees
16 Sept - 17 Sept
Pristine Cozy Walkable Downtown 2BR Getaway
A balcony with a view of a lake, white railings, and outdoor furniture.

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

River Overlook - What a view from your deck!
Collinsville
10.0 out of 10, Exceptional, (26 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 NZ$532
includes taxes & fees
8 Sept - 9 Sept
River Overlook - What a view from your deck!
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

18. 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 NZ$512
includes taxes & fees
9 Sept - 10 Sept
Sun Filled Lake House Living
A modern kitchen with a marble island, bar stools, a stainless steel stove, and a decorative chandelier.

19. Cozy 2-bedroom apartment with movie theater.

Cozy 2-bedroom apartment with movie theater.
Agawam
9.0 out of 10, Wonderful, (2 reviews)
"cute place, a bit humid and no AC control but the movie room is cool"
United States
London R.
The price is NZ$522
includes taxes & fees
1 Sept - 2 Sept
Cozy 2-bedroom apartment with movie theater.
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

20. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is NZ$942
includes taxes & fees
21 Sept - 22 Sept
Treetop Hideaway in Tyringham
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"
William 2-night trip
Posted 4 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, 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 NZ$279 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?

Cozy Riverside Berkshires Retreat: This holiday home rental outside of Tolland is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and kitchenware, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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. Tolland State Forest and Hartland Town Hall 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.