Watertown holiday rentals

We found 235 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Watertown that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Watertown

Showing deals for:25 Dec - 1 Jan

Living Room
Sunset
Foyer
Bedroom 1: King
Exceptional
(9 reviews)

6-Acre Luxurious Country Home with Goddess Point Lookout

Woodbury

5% off
AU$18,680
for 7 nights, 1 home
AU$2,669 per night
includes taxes & fees
6-Acre Luxurious Country Home with Goddess Point Lookout
Private kitchen
Gorgeous sunsets every night
Movie room with 85" 4k screen and surround sound Sonos System
18' x 36' heated pool.
Exceptional
(56 reviews)

Litchfield County Four Season Country Paradise

Roxbury

8% off
AU$13,189
for 7 nights, 1 home
AU$1,884 per night
includes taxes & fees
Litchfield County Four Season Country Paradise
3rd sleeping area with ground-floor walkout
Summer; forest view
Winter; main room
Kitchen
Exceptional
(8 reviews)

Peaceful Wooded Retreat – Quiet Escape, Close to Wolcott Lakes

Waterbury

8% off
AU$4,079
for 7 nights, 1 cabin
AU$583 per night
includes taxes & fees
Peaceful Wooded Retreat – Quiet Escape, Close to Wolcott Lakes
Barn Style Home - Best Location! Views!
Exterior
Room
Large Flagstone Terraces, Gas BBQ, Heated Pool
Exceptional
(7 reviews)

"Kielwasser 5BR" 2Hrs NYC,Best Town,Restaurants! HeatedPool,BBQ,4FPs, PoshPadsCT

Washington Depot

26% off
AU$16,326
for 7 nights, 1 home
AU$2,332 per night
includes taxes & fees
"Kielwasser 5BR" 2Hrs NYC,Best Town,Restaurants! HeatedPool,BBQ,4FPs, PoshPadsCT
Front of Cottage 2024
small, covered front porch on cottage
Lovely rolling 8 Acre farmland is shared with the main house
New refrigerator, microwave, air fryer, coffee maker 2022
Exceptional
(9 reviews)

Clean & Bright 2 Bedroom Cottage shares 8 Acres

Southbury

16% off
AU$3,602
for 7 nights, 1 cottage
AU$515 per night
includes taxes & fees
Clean & Bright 2 Bedroom Cottage shares 8 Acres
Living area
Interior
Property grounds
Private kitchen
Very good
(5 reviews)

Gather your family at this country estate

Watertown

7% off
AU$4,026
for 7 nights, 1 home
AU$575 per night
includes taxes & fees
Gather your family at this country estate
Interior
Living area
Private kitchen
Living area
Exceptional
(6 reviews)

Litchfield Modern Farmhouse

Litchfield

7% off
AU$3,174
for 7 nights, 1 room
AU$453 per night
includes taxes & fees
Litchfield Modern Farmhouse
Interior
Private kitchen
Private kitchen
Room
Very good
(9 reviews)

Excellent Home Away From Home

Waterbury

15% off
AU$2,152
for 7 nights, 1 home
AU$307 per night
includes taxes & fees
Excellent Home Away From Home
Dining
Exterior
Private kitchen
Room
Exceptional
(21 reviews)

Charming 2-bedroom house centrally located in Bristol

Bristol

8% off
AU$1,818
for 7 nights, 1 home
AU$260 per night
includes taxes & fees
Charming 2-bedroom house centrally located in Bristol
Terrace/patio
Property grounds
Living area
Exterior
Exceptional
(15 reviews)

Cozy cottage with AC and lake access in charming Connecticut suburb.

Watertown

8% off
AU$2,100
for 7 nights, 1 cottage
AU$300 per night
includes taxes & fees
Cozy cottage with AC and lake access in charming Connecticut suburb.
Private kitchen
Exterior
Dining
Interior
Exceptional
(19 reviews)

Barn Apartment Hideaway

Washington Depot

15% off
AU$2,939
for 7 nights, 1 apartment
AU$420 per night
includes taxes & fees
Barn Apartment Hideaway
Kitchen
View of the Pond
Entryway Stairs
Living Room
Exceptional
(7 reviews)

Private Apartment in Southbury 101

Southbury

8% off
AU$2,327
for 7 nights, 1 apartment
AU$332 per night
includes taxes & fees
Private Apartment in Southbury 101
Outdoors
Open Concept Living Room, Dining Room, Kitchen
Queen Bedroom
Dining Room
Wonderful
(6 reviews)

Private Apartment in Southbury 102

Southbury

8% off
AU$2,117
for 7 nights, 1 apartment
AU$302 per night
includes taxes & fees
Private Apartment in Southbury 102

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    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The friendly area of Watertown awaits your stay

The parks and other outdoor surroundings create an inviting atmosphere in Watertown. This welcoming city has many special qualities. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Watertown

Are you searching for things to do during your stay? Venture out of your cosy holiday rental and experience everything that makes Watertown a fun place to get away to. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • The Christmas Shop (5.1 mi / 8.2 km)
  • Quassy Amusement Park (5.7 mi / 9.2 km)
  • Mount Southington Ski Area (10.1 mi / 16.3 km)
  • Lake Compounce (10.2 mi / 16.5 km)
  • Sunset Meadow Vineyards (13.8 mi / 22.2 km)
  • Hopkins Vineyard (13.9 mi / 22.4 km)

Exploring the natural features in Watertown

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Watertown is a great place to get outside. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Waterbury Green (5.3 mi / 8.5 km)
  • Bantam Lake (8.6 mi / 13.9 km)
  • White Memorial Conservation Center (9.5 mi / 15.4 km)
  • Litchfield Town Green (10.4 mi / 16.8 km)
  • Beacon Falls Town Recreation Field (11.4 mi / 18.4 km)
  • Harwinton Conservation and Recreation Area (11.6 mi / 18.7 km)

Transport to and around Watertown

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 8.9 mi (14.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Danbury, CT (DXR-Danbury Municipal), which is 25 mi (40.2 km) away.

Frequently asked questions

What is the best area to stay in Watertown when booking a holiday rental?
When considering a holiday rental in Watertown, Connecticut, the area surrounding the town centre is an excellent choice. This neighbourhood offers a charming blend of local amenities and easy access to several attractions. Visitors can enjoy the picturesque views at the nearby Lake Quassapaug, which is great for outdoor activities like fishing and boating. Additionally, the historic Watertown Green is a lovely spot to explore, showcasing the town's rich heritage and providing a pleasant atmosphere for leisurely strolls.In terms of properties, Watertown features a variety of options, from quaint cottages to more spacious family homes, suiting different tastes and budgets.
What is the most popular type of holiday rental accomodation in Watertown?
In Watertown, a variety of holiday rental options are available, with cottages, apartments, and holiday houses all being quite popular. These accommodations can be found throughout the charming town, often situated in peaceful neighbourhoods that provide a relaxed atmosphere. Most cottages and holiday houses typically include amenities such as fully equipped kitchens, comfortable living areas, and outdoor spaces for enjoying the serene surroundings. Apartments, on the other hand, offer a more compact alternative, often featuring modern furnishings and conveniences.
Are there any family house rentals in Watertown?
In Watertown, Connecticut, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area features spacious homes in neighbourhoods that offer easy access to local parks and recreational facilities. Many properties come equipped with full kitchens, allowing for convenient meal preparation, as well as comfortable living areas where families can unwind together.Nearby attractions include parks like the Watertown Recreation Department, which offers playgrounds and sports fields, superb for outdoor activities. Visitors can also explore the charming town centre, where shops and dining options await.
Can I rent a holiday home with a pool or hot tub in Watertown?
In Watertown, Connecticut, several holiday homes are available for rent that feature pools and hot tubs. This charming town offers a mix of residential and scenic areas, making it an appealing choice for travellers seeking relaxation and leisure. Many of these properties come equipped with private pools, hot tubs, and spacious outdoor patios, great for enjoying the warm weather. Inside, you can expect amenities such as fully equipped kitchens, comfortable living spaces, and modern conveniences like Wi-Fi and air conditioning.
Are there pet-friendly house rentals in Watertown?
In Watertown, Connecticut, there are several pet-friendly house rentals available for those looking to enjoy a comfortable stay with their furry companions. Many of these properties come equipped with essential amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like gardens or patios, which are ideal for pets to roam.The town itself offers a friendly atmosphere with nearby parks, such as Veterans Memorial Park, which features walking trails and open spaces where pets can enjoy some exercise. Additionally, the surrounding areas provide opportunities for outdoor activities, making it a great choice for pet owners seeking a relaxing getaway.
Are there any remote work holiday rentals in Watertown?
In Watertown, Connecticut, there are approximately 12 remote work holiday rentals available, making it a great choice for those needing to balance work and leisure. These rentals typically offer amenities that cater to remote workers, such as free Wi-Fi, dedicated work desks, and computer monitors, ensuring a productive environment.The town itself provides a charming atmosphere with local parks and recreational areas, superb for breaks away from work. Nearby points of interest include the scenic Lake Quassapaug, where visitors can enjoy outdoor activities, and the historic Watertown Town Hall, adding a touch of local culture to your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Watertown?
In Watertown, popular rental amenities include kitchens, allowing guests to prepare their own meals, and decks or patios for outdoor relaxation. Many properties also offer onsite parking, which is convenient for those travelling with a car. Additionally, some rentals feature porches or lanais, providing a lovely space to enjoy the fresh air. For those who enjoy cooking, it's common to find blenders available for preparing smoothies or other beverages.
When is the best time to visit Watertown for a holiday rental?
The best time to visit Watertown for a holiday rental is during the peak season from July to September, when the weather is warm and inviting, superb for outdoor exploration. This vibrant period attracts many visitors eager to experience the area's natural beauty and community events. With temperatures typically ranging from the mid-teens to low 30s Celsius, it's an ideal time for picnics in the parks, hiking trails, and enjoying the local festivals that celebrate the summer spirit.July stands out as the most popular month to book your stay, as the town buzzes with activity and offers numerous opportunities for sightseeing and leisure. Families and friends can take advantage of the long summer days to explore nearby attractions, including the scenic Lake Quassapaug, where swimming and boating provide refreshing ways to relax and enjoy the outdoors.For those seeking a more budget-friendly option, consider planning your visit in December. While it's a quieter month, it presents a unique charm with festive decorations and a chance to enjoy winter activities. This off-peak time allows for a more relaxed experience, superb for those who appreciate tranquillity and the opportunity to explore at their own pace.Ultimately, whether you prefer the lively option of summer or the peacefulness of winter, Watertown offers a range of experiences that cater to all tastes.
What are the top attractions in Watertown?
In Watertown, Connecticut, visitors can explore several attractions that highlight the area's natural beauty and historical significance. One of the key points of interest is the Watertown Historical Society, which offers insights into the local history through various exhibits and events. The nearby Mattatuck State Forest provides ample opportunities for outdoor activities such as hiking and birdwatching, allowing visitors to immerse themselves in nature.The town is also home to Lake Winnemaug, where residents and visitors alike enjoy fishing, boating, and picnicking along the scenic shores. For those interested in art and culture, the Brass Mill Centre in nearby Waterbury offers shopping and dining experiences, along with occasional community events.
Are all fees included in the Watertown holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Watertown holiday homes with parking?
Stayz offers a wide selection of holiday homes in Watertown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Watertown holiday homes?
You can find great discounts on holiday homes in Watertown on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Watertown holiday home booking on Stayz?
To find Watertown holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Watertown?
A long-stay holiday home in Watertown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Watertown holiday home?
Book your Watertown holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Watertown?
Prices for holiday homes in Watertown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Watertown to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.