A mountainous landscape with autumn foliage, a valley, and distant buildings.

Watertown Vacation Rentals

Where to?

Dates

November 2026

December 2026

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

In two months

In three months

In four months

Our top choices for Watertown vacation rentals

A two-story house with a porch, a front door with a wreath, and a small garden area.

1. Bear Retreat - 2-bedroom house in Waterbury

Waterbury

Radha

SAR 1,171 total

includes taxes & fees

7 Nov - 8 Nov

A spacious living room with large windows, a fireplace, and a view of the outdoors.

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

Watertown

Elizabeth H.

SAR 1,869 total

includes taxes & fees

11 Nov - 12 Nov

A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

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

Waterbury

Dirk N.

SAR 520 total

includes taxes & fees

8 Nov - 9 Nov

A building entrance with a brick facade, a green awning, and a glass door.

4. Cozy Studio apartment in delightful Waterbury with Central Air

Waterbury

"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.."

zynaisha

SAR 377 total

includes taxes & fees

2 Dec - 3 Dec

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

Oakville

SAR 2,023 total

includes taxes & fees

9 Nov - 10 Nov

A white house with a wooden staircase leading to a porch.

6. Cozy One Bedroom Apartment Centrally Located in Southbury

Southbury

Lisbeth

SAR 492 total

includes taxes & fees

1 Dec - 2 Dec

A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

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

Morris

Joe K.

SAR 992 total

includes taxes & fees

8 Nov - 9 Nov

A view through a window with a clear sky and lush greenery outside.

8. Private Apartment in Southbury 101

Southbury

Marissa G.

SAR 1,012 total

includes taxes & fees

1 Dec - 2 Dec

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

Wolcott

David G.

SAR 1,440 total

includes taxes & fees

30 Nov - 1 Dec

A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

10. Private Apartment in Southbury 104

Southbury

Daniel R.

SAR 999 total

includes taxes & fees

6 Dec - 7 Dec

A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

11. Private Apartment in Southbury 102

Southbury

Debbie P.

SAR 944 total

includes taxes & fees

30 Nov - 1 Dec

A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

12. The Jefferson Guest House, Spacious, Special Views

Litchfield

Jennifer A.

SAR 1,354 total

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a front porch, a small balcony, and a white picket fence.

13. Cozy Attic 10 min to Llitchfield

Torrington

Nicole N.

SAR 1,328 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

14. Cozy private room in a shared home with a Full-size bed and private bathroom.

New Milford

Jim B.

SAR 490 total

includes taxes & fees

9 Nov - 10 Nov

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!

Morris

Shannon M.

SAR 1,825 total

includes taxes & fees

18 Nov - 19 Nov

A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

16. The Sun Filled Cozy Creamery

Plainville

Heather T.

SAR 877 total

includes taxes & fees

29 Nov - 30 Nov

17. Cozy Modern Farmhouse Private Apt - 3 Beds

Torrington

Louisa A.

SAR 1,525 total

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a sectional sofa, a coffee table, and a kitchen in the background.

18. #23 COMFORT & LUXURY 3 BR/2 BA House

Southington

Lynn O.

A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

19. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Southington

"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."

Cindy M.

SAR 1,869 total

includes taxes & fees

8 Nov - 9 Nov

A modern living room with a dark sofa, a small side table, and a kitchen area with a refrigerator and microwave.

20. Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Cheshire

James P.

View all properties

Find vacation rentals that suit your style

Top Watertown Hotel Reviews

A hotel lobby with a modern design, featuring a seating area with sofas, a fireplace, and a television mounted on the wall.

Courtyard by Marriott Waterbury Downtown

Waterbury

10/10 Excellent

Courtney

A covered porch with white columns and black hanging lanterns.

The Milestone Inn

Woodbury

10/10 Excellent

Elin

A spacious hotel lobby with wooden beams, a central seating area, and large windows offering a view.

Heritage Hotel, Golf & Conference Center

Southbury

10/10 Excellent

Always a good stay. Been coming to this hotel with the family for at least a decade and I also worked here in my young adult life. The staff is always pleasant, the place is always clean. The pool was a little overcrowded for once and we were given wrist bands for the first time ever. There was a staff member checking we had them on yet 75% of the people there did not have them which I thought was odd. We did not get too enjoy the pool as much as we would have wanted, it’s a great pool but there...

Luz

A restaurant with wooden tables and chairs, a bar area, and hanging spherical light fixtures.

The Abner Hotel

Litchfield Historic District

10/10 Excellent

Karen

An outdoor seating area with fire pits and umbrellas, surrounded by modern buildings with large windows.

DoubleTree by Hilton Hotel Bristol, Connecticut

Bristol

10/10 Excellent

Susan

An outdoor patio with a fire pit, wicker furniture, and a pergola structure.

Homewood Suites by Hilton Southington, CT

Southington

10/10 Excellent

Suzanne Martin

An outdoor patio area with a fire pit and seating, surrounded by a building with large windows and a parking lot.

Courtyard by Marriott Southington

Southington

10/10 Excellent

Christopher

A breakfast buffet area with various food options and a bakery section.

Holiday Inn Express Southington by IHG

Southington

10/10 Excellent

Steffani

A large, two-story house with a wrap-around porch, a central entrance, and a flag.

Belden House & Mews

Litchfield Historic District

10/10 Excellent

Anthony

A hotel room with a bed, bedside tables, a desk, a chair, a lamp, and a window.

Hampton Inn & Suites By Hilton North Haven

North Haven

10/10 Excellent

Leontia S

A Holiday Inn hotel with a covered entrance, multiple floors, and a well-lit facade.

Holiday Inn Cheshire - Southington by IHG

Southington

10/10 Excellent

I liked this hotel. The area was quiet, the staff was professional and the hotel was clean. My only setback was the keycard kept having issues so I had to make trips to front desk. Apart from that, the stay was fine and I would go back. Parking was always available. The hotel sold bkfast and lunches, but also offered free coffee all day. There were food places, including fast foods and diners, that were literally 2‐4 minutes away which was very convenient for the stay.

Constantia

Frequently Asked Questions

Can I find vacation rentals in Watertown?

Yes, we have vacation rentals near top points of interest in Watertown, or you can choose a more secluded option if you want a relaxing place to stay. Watertown is known for its parks.

What are some of the best vacation home rentals in Watertown?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental outside of Watertown offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Watertown?

Expedia has 6 vacation rentals for your stay in Watertown.

What’s there to see and do in Watertown?

Explore the area and family-friendly sights such as The Christmas Shop, or get out into nature at a spot like Lake Winnemaug. In the larger area, you’ll find Black Rock State Park and Abbey of Regina Laudis.

What’s a vacation rental in Watertown like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Watertown. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.

Watertown Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Watertown vacation rentals

1. Bear Retreat - 2-bedroom house in Waterbury

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

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

4. Cozy Studio apartment in delightful Waterbury with Central Air

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

6. Cozy One Bedroom Apartment Centrally Located in Southbury

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

8. Private Apartment in Southbury 101

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

10. Private Apartment in Southbury 104

11. Private Apartment in Southbury 102

12. The Jefferson Guest House, Spacious, Special Views

13. Cozy Attic 10 min to Llitchfield

14. Cozy private room in a shared home with a Full-size bed and private bathroom.

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

16. The Sun Filled Cozy Creamery

17. Cozy Modern Farmhouse Private Apt - 3 Beds

18. #23 *COMFORT & LUXURY* 3 BR/2 BA House

19. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

20. Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Find vacation rentals that suit your style

Top Watertown Hotel Reviews

Courtyard by Marriott Waterbury Downtown

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Watertown?

What are some of the best vacation home rentals in Watertown?

How many vacation rentals are there in Watertown?

What’s there to see and do in Watertown?

What’s a vacation rental in Watertown like?

18. #23 COMFORT & LUXURY 3 BR/2 BA House