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Tolland Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Tolland holiday rentals

A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

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 HK$1,243
HK$1,564 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Camper tucked into the woods
A house with a porch, a garden with pink flowers, and a stone wall along the road.

2. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (153 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 HK$1,538
HK$2,820 total
includes taxes & fees
22 Oct - 23 Oct
Big farmhouse in the foothills of the Berkshires
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

3. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (55 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is HK$1,923
HK$4,515 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Cottage-Sunset On The Lake
A square fire pit with flames, surrounded by a grassy field and a green chair.

4. 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 HK$735
HK$1,453 total
includes taxes & fees
28 Oct - 29 Oct
Peaceful Meadow Retreat
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 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 HK$581
HK$2,498 total
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
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, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,257
HK$3,087 total
includes taxes & fees
28 Oct - 29 Oct
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 HK$1,144
HK$2,944 total
includes taxes & fees
27 Oct - 28 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A wooden cabin interior with a bench, a rug, and a hanging plant.

8. 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, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is HK$903
HK$1,654 total
includes taxes & fees
1 Nov - 2 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

9. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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 HK$2,103
HK$4,397 total
includes taxes & fees
17 Nov - 18 Nov
Treetop Hideaway in Tyringham
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

10. 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, (9 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is HK$883
HK$1,293 total
includes taxes & fees
26 Oct - 27 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
A hotel room with a bed, a nightstand, a lamp, and a wardrobe.

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 HK$613
HK$705 total
includes taxes & fees
1 Nov - 2 Nov
1 Queen Bed | Micfridge
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

12. 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 HK$534
HK$2,045 total
includes taxes & fees
26 Oct - 27 Oct
Sun Filled Lake House Living
A hotel lobby with a reception desk, a seating area with chairs and a table, and a large window providing natural light.

13. 1 Queen Bed | ADA/Tub/Micfridge

1 Queen Bed | ADA/Tub/Micfridge
Windsor Locks
10.0 out of 10, Exceptional, (53 reviews)
"Quiet room, easy check-in, slept well after a long flight."
United States
Anonymous traveller
The price is HK$613
HK$705 total
includes taxes & fees
1 Nov - 2 Nov
1 Queen Bed | ADA/Tub/Micfridge
A balcony with a view of a lake, white railings, and outdoor furniture.

14. 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 HK$1,397
HK$2,640 total
includes taxes & fees
25 Oct - 26 Oct
River Overlook - What a view from your deck!
A cozy room with two beds, large windows, and a view of a snowy landscape.

15. 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 HK$1,413
HK$2,174 total
includes taxes & fees
3 Nov - 4 Nov
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.

16. 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 HK$725
HK$2,782 total
includes taxes & fees
3 Nov - 4 Nov
Cozy Attic 10 min to Llitchfield
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

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

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
9.0 out of 10, Wonderful, (2 reviews)
"Lots of care provided for guests. We unfortunately did not have opportunity to take advantage of many of the amenities but enjoyed our stay."
United States
Judy L.
The price is HK$1,370
HK$1,733 total
includes taxes & fees
2 Nov - 3 Nov
Collinsville River Escape / Fall Foliage, Deck & Yard
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
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 HK$1,766
HK$2,735 total
includes taxes & fees
21 Oct - 22 Oct
Cozy 2-bedroom apartment with movie theater.
A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

19. The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is HK$573
HK$2,100 total
includes taxes & fees
4 Nov - 5 Nov
The Historic Hideaway
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

20. 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 HK$1,123
HK$3,433 total
includes taxes & fees
3 Nov - 4 Nov
Art House 3 Beds Close to Warner Theater
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"
Hope 1-night trip
Posted 8 hours ago
The Red Lion Inn

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:

  • View our selection of featured holiday rentals in Tolland
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  • Enter your travel dates to view the best deals on holiday rentals in Tolland while they last

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

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.