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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Thomaston holiday rentals

A wooden deck with lounge chairs and a railing overlooking a body of water at sunset.

1. Sunset Cove Lakefront Retreat with Private Dock

Sunset Cove Lakefront Retreat with Private Dock
Plymouth
Sunset Cove Lakefront Retreat with Private Dock
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, (16 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AU$386
includes taxes & fees
17 Sept - 18 Sept
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A spacious living room with large windows, a fireplace, and a view of the outdoors.

3. 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 AU$755
includes taxes & fees
17 Sept - 18 Sept
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

4. 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 AU$521
includes taxes & fees
21 Sept - 22 Sept
The Jefferson Guest House, Spacious, Special Views
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)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
United States
Elizabeth H.
The price is AU$757
includes taxes & fees
17 Sept - 18 Sept
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
A bunk bed with a ladder, a bedside table, a lamp, and a window with curtains.

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

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
The price is AU$1,183
includes taxes & fees
1 Oct - 2 Oct
Lakehaven • Hot Tub, Decks, Fires & More
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

7. 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 AU$174
includes taxes & fees
21 Sept - 22 Sept
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

8. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"It was great!"
United States
Amanda T.
The price is AU$402
includes taxes & fees
20 Sept - 21 Sept
Pristine Cozy Walkable Downtown 2BR Getaway
A front view of a house with a wooden staircase leading to a front door, a small porch area, and a garage door.

9. 1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is AU$546
includes taxes & fees
1 Oct - 2 Oct
1-bedroom vacation home 22 minutes from Quinnipiac University
A bedroom with a large bed, a wooden door, a mirror, and a wall-mounted light fixture.

10. Bristol Condo Near ESPN HQ & Lake Compounce!

Bristol Condo Near ESPN HQ & Lake Compounce!
Bristol
The price is AU$430
includes taxes & fees
27 Sept - 28 Sept
Bristol Condo Near ESPN HQ & Lake Compounce!
A patio with a table and chairs, a grill, and a view of a lake.

11. 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)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AU$670
includes taxes & fees
17 Sept - 18 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A spacious living room with a brown leather sofa, a dining area with a wooden table and chairs, and a kitchen with stainless steel appliances.

12. #11 - 4 Bedrooms, 3 Baths! Sleeps up to 8

#11 - 4 Bedrooms, 3 Baths! Sleeps up to 8
Plainville
10.0 out of 10, Exceptional, (3 reviews)
"Great weekend with friends!"
United States
Neil R.
#11 - 4 Bedrooms, 3 Baths! Sleeps up to 8
A loft-style room with a sloped ceiling, a wooden beam, a TV, a white entertainment unit, a black chair, a small table, and a lamp.

13. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is AU$440
includes taxes & fees
25 Sept - 26 Sept
Bristol Condo Near Espn HQ & Lake Compounce!
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 AU$591
includes taxes & fees
7 Oct - 8 Oct
Cozy Modern Farmhouse Private Apt - 3 Beds
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

15. 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 AU$821
includes taxes & fees
17 Sept - 18 Sept
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

16. 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 AU$593
includes taxes & fees
17 Sept - 18 Sept
Art House 3 Beds Close to Warner Theater
A two-story house with a front porch, a small balcony, and a white picket fence.

17. 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 AU$495
includes taxes & fees
7 Oct - 8 Oct
Cozy Attic 10 min to Llitchfield
A balcony with a view of a lake, white railings, and outdoor furniture.

18. 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 AU$427
includes taxes & fees
27 Sept - 28 Sept
River Overlook - What a view from your deck!
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, (36 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is AU$173
includes taxes & fees
20 Sept - 21 Sept
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

20. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$410
includes taxes & fees
17 Sept - 18 Sept
Once the old Schools house now a newly furnished Apartment
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

Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

8/10 Good
"Las instalaciones están lindas para pasar un día en el hotel ayuda mucho y tiene cerca varios fast food"
Leidi 1-night trip
Posted 12 hours ago
Clarion Inn North Haven - New Haven North

Find out more about Thomaston

Everything you need to know about Thomaston 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 Thomaston 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 Thomaston holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Thomaston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Thomaston. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Thomaston 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 Thomaston holiday rentals we have selected for you start as low as AU$427 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Thomaston rentals

At Expedia, we put the best Thomaston 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 Thomaston 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 Thomaston 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 Thomaston. 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

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.