A railway track curving through a forested hillside.

Thomaston Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Thomaston holiday rentals

A modern interior with a central light fixture, seating arrangement, and large windows.

1. Coming Soon! #32- Sleeps 10!

Coming Soon! #32- Sleeps 10!
Plymouth
8.0 out of 10, Very good, (1 review)
"Everything was great, just 2 things… Is only 1 tv for the whole apartment, and there is another apartment upstairs and you can hear everything….other than that everything was great."
United States
Humberto H.
Coming Soon! #32- Sleeps 10!
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

2. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (18 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is HK$1,686
HK$2,096 total
includes taxes & fees
30 Sept - 1 Oct
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

3. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
The price is HK$2,415
HK$2,909 total
includes taxes & fees
1 Oct - 2 Oct
The Jefferson Guest House, Spacious, Special Views
A spacious living room with large windows, a fireplace, and a view of the outdoors.

4. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is HK$2,141
HK$4,228 total
includes taxes & fees
11 Oct - 12 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A spacious living room with large windows, a fireplace, and a view of the outdoors.

5. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown
9.0 out of 10, Wonderful, (6 reviews)
The price is HK$1,718
HK$4,016 total
includes taxes & fees
12 Oct - 13 Oct
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

6. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (21 reviews)
"It was great!"
United States
Amanda T.
The price is HK$1,260
HK$2,164 total
includes taxes & fees
30 Sept - 1 Oct
Pristine Cozy Walkable Downtown 2BR Getaway
A two-story house with a front porch, a small balcony, and a white picket fence.

7. 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 HK$1,013
HK$3,194 total
includes taxes & fees
30 Sept - 1 Oct
Cozy Modern Farmhouse Private Apt - 3 Beds
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

8. 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$1,073
HK$3,174 total
includes taxes & fees
30 Sept - 1 Oct
Art House 3 Beds Close to Warner Theater
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

9. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is HK$1,871
HK$4,396 total
includes taxes & fees
30 Sept - 1 Oct
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A two-story house with a front porch, a small balcony, and a white picket fence.

10. 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 HK$708
HK$2,620 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Attic 10 min to Llitchfield
A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

11. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
The price is HK$863
HK$1,149 total
includes taxes & fees
30 Sept - 1 Oct
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

12. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$777
HK$1,050 total
includes taxes & fees
5 Oct - 6 Oct
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A living room with a sectional sofa, a small side table, and a floor lamp.

13. Lakehaven • Hot Tub, Decks, Fires & More

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
The price is HK$2,718
HK$6,742 total
includes taxes & fees
1 Oct - 2 Oct
Lakehaven • Hot Tub, Decks, Fires & More
A deck with a white chair and a table, a sliding glass door, and a potted plant.

14. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is HK$1,373
HK$2,461 total
includes taxes & fees
7 Oct - 8 Oct
Bristol Condo Near Espn HQ & Lake Compounce!
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

15. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (4 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is HK$2,275
HK$4,213 total
includes taxes & fees
5 Oct - 6 Oct
Escape to Bantam Lake- With Fireplace and Hot tub!
A two-story house with a porch, a front door with a wreath, and a small garden area.

16. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is HK$918
HK$2,475 total
includes taxes & fees
8 Oct - 9 Oct
Bear Retreat - 2-bedroom house in Waterbury
A patio with a table and chairs, a grill, and a view of a lake.

17. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (72 reviews)
"Wow! What a great place! The house is lovely, very clean, comfy beds and cozy seating. Amazing view and an unbeatable location!"
United States
Kristi M.
The price is HK$2,203
HK$3,623 total
includes taxes & fees
30 Sept - 1 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A compact kitchen with wooden cabinets, a microwave, a sink, and a chair.

18. Cozy Studio apartment in delightful Waterbury with Central Air

Cozy Studio apartment in delightful Waterbury with Central Air
Waterbury
2.0 out of 10, (1 review)
"The place wasn’t how the pictures were on the app. It was hard to find the room. The keys for the room are very hard to open the room door . It’s like you have to struggle just to get inside . The room is inside of an abandoned building… some staff in the building was telling me that I shouldn’t be staying there or they wouldn’t stay there so it made me feel unsafe… the bed doesn’t match the head board. Everything just doesn’t match the images the host posted.."
United States
zynaisha
The price is HK$530
HK$766 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Studio apartment in delightful Waterbury with Central Air
A white house with a wooden staircase leading to a porch.

19. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is HK$671
HK$928 total
includes taxes & fees
13 Oct - 14 Oct
Cozy One Bedroom Apartment Centrally Located in Southbury
A spacious room with a wooden staircase, a dining area with chairs and a table, and a large window with a view of trees.

20. Bristol Condo Near ESPN HQ & Lake Compounce!

Bristol Condo Near ESPN HQ & Lake Compounce!
Bristol
The price is HK$1,035
HK$2,367 total
includes taxes & fees
3 Oct - 4 Oct
Bristol Condo Near ESPN HQ & Lake Compounce!
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 Thomaston Hotel Reviews

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

8/10 Good
"Thumbs down on the breakfast"
Paula 2-night trip
Posted 15 hours ago
Homewood Suites by Hilton Hartford-Farmington

Find out more about Thomaston

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

  • View our selection of featured holiday rentals in Thomaston
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Look no further and take a look at our great range of rental properties in Thomaston!

Frequently asked questions

Can I find a holiday rental in Thomaston?

Yes, there are holiday rentals close to the most popular sights in Thomaston, 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 Thomaston has to offer?

Well laid out 2-bedroom private home in Washington-close to the green and depot: This holiday home rental outside of Thomaston offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. Make the most of garden in this rental home to help you unwind.

What’s there to see and do in Thomaston?

Explore the area and family-friendly sights such as The Christmas Shop, or get out into nature at a spot like Harwinton Conservation and Recreation Area. In the wider area, you’ll find Black Rock State Park and New England Carousel Museum.

What’s a holiday rental in Thomaston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Thomaston. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family trips.