A railway track curving through a forested hillside.

Thomaston Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Thomaston holiday rentals

Coffee/tea maker, fridge, microwave, oven

1. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is HK$2,288
HK$2,979 total
includes taxes & fees
3 Sept - 4 Sept
The Jefferson Guest House, Spacious, Special Views
Interior

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, (13 reviews)
"The property was very clean and inviting and the owner was very welcoming and helpful!"
United States
Sarah
The price is HK$1,687
HK$2,183 total
includes taxes & fees
16 Aug - 17 Aug
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Interior

3. #11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Plainville
10.0 out of 10, Exceptional, (3 reviews)
"Great weekend with friends!"
United States
Neil R.
The price is HK$2,762
HK$5,366 total
includes taxes & fees
15 Aug - 16 Aug
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Dining

4. 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$1,836
HK$4,088 total
includes taxes & fees
24 Aug - 25 Aug
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Coffee/tea maker, fridge, microwave, oven

5. #26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (5 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is HK$1,444
HK$2,579 total
includes taxes & fees
15 Aug - 16 Aug
#26 Beautifully Renovated 2 BR Home
Outdoor dining

6. 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, (68 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is HK$2,448
HK$4,172 total
includes taxes & fees
17 Aug - 18 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Smart TV, fireplace

7. 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 HK$1,334
HK$2,282 total
includes taxes & fees
1 Sept - 2 Sept
Pristine Cozy Walkable Downtown 2BR Getaway
Interior

8. 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
8.8 out of 10, Excellent, (11 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$855
HK$1,141 total
includes taxes & fees
8 Sept - 9 Sept
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Coffee/tea maker, fridge, microwave, oven

9. #27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is HK$3,518
HK$6,118 total
includes taxes & fees
29 Aug - 30 Aug
#27- Luxury Collection
TV

10. #43- Modern Luxury Log Cabin Retreat | Fire Pit

#43- Modern Luxury Log Cabin Retreat | Fire Pit
Prospect
9.0 out of 10, Wonderful, (2 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
The price is HK$2,510
HK$4,770 total
includes taxes & fees
15 Aug - 16 Aug
#43- Modern Luxury Log Cabin Retreat | Fire Pit
Coffee/tea maker, fridge, microwave, oven

11. #16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (8 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
The price is HK$2,511
HK$4,818 total
includes taxes & fees
7 Sept - 8 Sept
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Exterior

12. 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$2,645 total
includes taxes & fees
1 Sept - 2 Sept
Cozy Modern Farmhouse Private Apt - 3 Beds
Exterior

13. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.4 out of 10, Exceptional, (6 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is HK$742
HK$2,230 total
includes taxes & fees
1 Sept - 2 Sept
Cozy Attic 10 min to Llitchfield
Dining

14. 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$1,103
HK$3,407 total
includes taxes & fees
1 Sept - 2 Sept
Art House 3 Beds Close to Warner Theater
Smart TV

15. #23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (9 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is HK$2,510
HK$4,456 total
includes taxes & fees
29 Aug - 30 Aug
#23 *COMFORT & LUXURY* 3 BR/2 BA House
Property grounds

16. 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 HK$1,165
HK$2,366 total
includes taxes & fees
17 Aug - 18 Aug
River Overlook - What a view from your deck!
Coffee/tea maker, fridge, microwave, oven

17. #10 *THE ULTIMATE AIRBNB GETAWAY!*

#10 *THE ULTIMATE AIRBNB GETAWAY!*
Southington
9.0 out of 10, Wonderful, (2 reviews)
"A great place to stay with family. The great room was an xtra bonus and surprise for all with lots of room!"
United States
Susan N.
The price is HK$2,427
HK$4,933 total
includes taxes & fees
19 Aug - 20 Aug
#10 *THE ULTIMATE AIRBNB GETAWAY!*
Interior

18. #3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Plainville
8.8 out of 10, Excellent, (15 reviews)
"Great place and good location."
United States
MARC S.
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Dining

19. Prime West Hartford Center: Timeless Charm

Prime West Hartford Center: Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (24 reviews)
"Great location and lots of room for grandkids to spread out and fun games for them to play with"
United States
Michael W.
The price is HK$2,246
HK$4,329 total
includes taxes & fees
14 Sept - 15 Sept
Prime West Hartford Center: Timeless Charm
TV, fireplace

20. #41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
The price is HK$2,762
HK$5,366 total
includes taxes & fees
26 Aug - 27 Aug
#41- Available 12/8! - sleeps 14
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Thomaston Hotel Reviews

Red Roof Inn Meriden

Red Roof Inn Meriden

10/10 Excellent
"Abitacion limpia precio justo"
Gamaliel 1-night trip
Posted 5 hours ago
Red Roof Inn Meriden

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
  • Use the map to find apartments and other holiday homes in the Thomaston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Thomaston while they last

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.