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Watertown Holiday Rentals

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Our top choices for Watertown holiday rentals

Holiday Home in Watertown

9.6 out of 10, Exceptional, (16)
"It was a great time. Loved it hear would come back again. Owner was very helpful."
United States
Nosa I.
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Holiday Home in Brookfield

9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Holiday Home in New Fairfield

9.2 out of 10, Wonderful, (34)
"It’s a great place to stay for the weekend. Has all the things you want to do to relax by the lake. "
United States
Meredith R.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Holiday Home in Plymouth

9.8 out of 10, Exceptional, (40)
"Our stay was so peaceful and relaxing. The property was beautiful and exactly as described in the listing. We loved having a fire outside, sitting in the screened-in porch. Will absolutely be coming back!"
United States
Jean R.
Cozy Lakefront Bungalow w firepit/dock/kayaks

Apartment in Cheshire

9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Cabin in Northwest Harwinton

8.8 out of 10, Excellent, (28)
"Great little place, beutiful view to enjoy your coffee."
United States
Shaun H.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Holiday Home in West Hartford

2.0 star property
8.6 out of 10, Excellent, (9)
"Great house in a safe neighborhood with a fenced in yard. Amenities provided. "
United States
Ben H.
The price is AU$463
includes taxes & fees
18 Dec - 19 Dec
Charming 3-Bedroom Home with Modern Comforts in West Hartford

Holiday Home in Berlin

2.0 star property
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is AU$481
includes taxes & fees
14 Dec - 15 Dec
Private Apartment in Berlin

Holiday Home in New Britain

10.0 out of 10, Exceptional, (8)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
The price is AU$375
includes taxes & fees
14 Dec - 15 Dec
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Holiday Home in Danbury

10.0 out of 10, Exceptional, (24)
"Beautiful property with amazing lake views and water access."
United States
Sophia C.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Holiday Home in Goshen

9.6 out of 10, Exceptional, (42)
"The place was very nice met all of our expectations. "
United States
Marie G.
The Goshen Glass Chalet

Apartment in Southbury

9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is AU$189
includes taxes & fees
14 Dec - 15 Dec
New One Bedroom Apartment Centrally Located in Southbury

Apartment in West New Haven

2.0 star property
9.4 out of 10, Exceptional, (3)
"Great communication and easy check in, would recommend "
United States
Ethan R.
The price is AU$198
includes taxes & fees
16 Dec - 17 Dec
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Holiday Home in New Fairfield

10.0 out of 10, Exceptional, (80)
"Beautiful fun home, great owner!"
United States
Robin B.
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

Holiday Home in Cornwall

9.6 out of 10, Exceptional, (53)
"Great house and great stay!"
United States
Timothy P.
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Holiday Home in New Fairfield

9.8 out of 10, Exceptional, (35)
"Perfect location, well equipped from decks and dock, kayaks and fire pit. Beautiful well kept landscape. Nice open floor plan for family gatherings."
United States
Brian W.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Holiday Home in New Fairfield

2.0 star property
9.8 out of 10, Exceptional, (7)
"Great spot "
United States
Mike P.
The price is AU$1,172
includes taxes & fees
6 Jan - 7 Jan 2026
Awesome Lake Home with tons of fun!

Holiday Home in Shelton

9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is AU$300
includes taxes & fees
14 Dec - 15 Dec
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Apartment in Wallingford Center

9.8 out of 10, Exceptional, (6)
"I highly recommend this property!! We were in town for a wedding celebration, and it proved perfect. The property is completely updated, well-appointed and clean. The property is centrally located and close to restaurants, shops and grocery markets. Karl was a great host and communicated with us throughout our stay. I highly recommend!!"
United States
Francis S.
The price is AU$439
includes taxes & fees
18 Dec - 19 Dec
All New 1BR with tons of Charm

Holiday Home in New Fairfield

10.0 out of 10, Exceptional, (16)
"The house worked very well for our family holiday. Very clean, had everything we needed "
United States
Audrey P.
The price is AU$792
includes taxes & fees
15 Dec - 16 Dec
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
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 Watertown Hotel Reviews

Find out more about Watertown

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

Watertown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Watertown. 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 Watertown 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 Watertown holiday rentals we have selected for you start as low as AU$189 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Watertown rentals

At Expedia, we put the best Watertown 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 Watertown 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 Watertown 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 Watertown. 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 holiday rentals in Watertown?

Yes, there are holiday rentals close to the most popular sights in Watertown, or you can select a more secluded option if you're looking for a relaxing stay. Watertown is known for its parks.

What are some of the best holiday rentals that Watertown has to offer?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit: This holiday home rental outside of Watertown is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Watertown?

Expedia has 3 holiday 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 Hollow Park. In the wider area, you’ll find Black Rock State Park and Abbey of Regina Laudis.

What’s a holiday rental in Watertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Watertown. Holiday rentals offer extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for small groups.