Holiday rentals in Naugatuck Valley Planning Region

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Top-rated holiday rentals in Naugatuck Valley Planning Region

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Waterbury
4.96 out of 5 average rating, 155 reviews

Amazing views of the Brass City

East Mountain Views at its finest. This clean, 3-bedroom updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (July). Wi-Fi/cable, central AC/hot air, washer/dryer, and patio furniture/grill (seasonal) are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey) are provided. This house is truly relaxing and will feel like home.

Guest favourite
A spacious living area is presented with a large flat-screen TV mounted on a white entertainment unit. A soft gray sofa sits nearby, and a decorative area rug enhances the room's aesthetic. Natural light streams in through a front door adorned with a glass panel.
Guest house in Watertown
4.94 out of 5 average rating, 117 reviews

Private studio guesthouse

Kick back and relax in this peaceful, quiet, stylish space with high ceilings, central heat and air, huge bathroom, mini kitchen, fridge, microwave, coffee maker, 75" TV, onsite laundry and workout equipment when needed, private parking space, private entrance, high-speed internet, countless local restaurants, fast food chains and cafes, all major supermarkets, hospitals and doctors offices, post offices, easy access to numerous lakes, golf course and wineries. Indeed, a home away from home.

Guest favourite
A cozy living room features a stone fireplace with a mounted television above. Natural light enters through a large window, accented by sheer curtains. A plush rug covers the floor, surrounded by a sectional sofa and a chair, offering a comfortable gathering space.
Home in Waterbury
4.95 out of 5 average rating, 103 reviews

Come and enjoy the BURY's of CT!

Welcome to your home away from home! Nestled in a charming, safe, and quiet neighborhood, our cozy retreat offers the perfect blend of comfort and convenience. You'll love the tree-lined streets and peaceful atmosphere—a perfect place to relax after a day of exploring. Whether you're here for business or leisure, our home provides a warm and welcoming space in a delightfully cute corner of town. Enjoy all that CT has to offer from the rolling hills of Litchfield to the waters of the sound.

Top guest favourite
A newly renovated barn features a dark exterior with large windows on both levels. A gravel patio area is surrounded by low shrubs, providing a space with a table and chairs for outdoor dining. Lush green trees frame the serene setting.
Barn in Roxbury
5 out of 5 average rating, 100 reviews

Fully Renovated Rural Barn

Newly renovated barn on a quiet rural road yet close to all the attractions of Southern Litchfield County. The light-filled barn has two large patio doors into a substantial living and entertaining area with a large sectional sofa-bed, a dining table for 10 and adjacent kitchen area with an island. There is a downstairs washroom. A large light-filled upstairs sleeping area has a king-size bed and a bathroom with shower. Outside is a patio dining area and parking in a dedicated driveway.

Top guest favourite
Flat in Southbury
4.97 out of 5 average rating, 102 reviews

Cozy Apartment Centrally Located in Southbury

Keep it simple at this peaceful and centrally-located apartment. Recently renovated with all the essential amenities to make your stay just like home. Wi-Fi, washer, dryer, cooktop, fridge, oven, microwave, toaster, TV and Keurig are ready to make your stay pleasant. An outdoor porch is available for dining in warmer months. It includes one new queen bed plus sofa bed for one adult or two kids. Located just minutes from shopping and dining in downtown Southbury with easy access to i84

Top guest favourite
A timber-style cottage is surrounded by landscaping featuring stones and low shrubs. A spacious deck with white railings leads to a welcoming entrance. Light-colored siding and multiple windows enhance the two-story structure, set against a backdrop of trees and open land.
Home in Southbury
4.98 out of 5 average rating, 168 reviews

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm, a one bedroom, one bath cottage located on a 16 acre working Christmas tree farm bordered by 155 acres of protected land trust with marked hiking trails. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village. Please note that we allow pets (dogs only) and have a limit of two. **Access to the 2nd floor bedroom is a steep and open staircase** (see interior photo listed under Laundry)

Top guest favourite
A spacious deck features a round table surrounded by four cushioned chairs, covered by a large red umbrella. Lush greenery and landscaped gardens are visible in the background, creating a serene outdoor setting.
Cottage in Seymour
4.96 out of 5 average rating, 130 reviews

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

Top guest favourite
A rustic exterior of a large studio is framed by trees showcasing fall colors. The structure features a unique design with a gabled roof and wooden paneling. A gravel driveway and a stone patio are visible, providing access to the entrance amid a serene natural setting.
Guest house in Southbury
4.93 out of 5 average rating, 90 reviews

The Nest. Large studio in the Woods.

New large studio on secluded property at the end of the country road. Surrounded by trees and across the river from the National Audubon, bird sanctuary. 5 minutes from I-84. 4 minutes from town and 1 hour from Manhattan. Private, peaceful and restful. If you want to retreat to nature and rejuvenate your spirit this is the place for you. We look forward to hosting you in this lovely setting and sharing our favorite list of walking trails.

Top guest favourite
Flat in Middlebury
4.94 out of 5 average rating, 161 reviews

Cozy Apartment with Water View of Brook

Lower Level Beautiful Space: Well kept with an amazing view of a Beautiful Brook that Runs through the Backyard. It is a small cottage style home and you will have the best views of the Brook. You will also hear and see the Brook from the Bedroom, Kitchenette and Patio. Depending on the season it will Vary. If you have 2 Cars please make sure you let me know so I can accommodate.

Top guest favourite
A spacious living area features large windows allowing natural light to fill the room. A sectional sofa and armchair are arranged around a decorative rug. A television is positioned on a wooden cabinet, and a plant adds a touch of greenery to the decor.
Flat in New Haven
4.94 out of 5 average rating, 124 reviews

Apartment in New Haven

This is a luxurious and spacious apartment on the ground floor of a historic home, centrally located in the heart of East Rock. It is a 5 min drive (or 20 min walk) from Yale's campus and there is a shuttle stop right next to the house on Whitney (blue/orange lines). The master bedroom has a king bed and a private shower/bathroom. The guest bedroom has a queen bed and library.

Guest favourite
Guest suite in Watertown
4.83 out of 5 average rating, 48 reviews

Modern Ranch style apartment.

Escape to a stylish accommodation at this centrally located Basement apartment.Come experience spacious and refined living for your ultimate comfort. Lodged in a quiet neighborhood, it's only 15mins to shopping amenities. This is your "Home Away from Home". Apartment is located next to a farm, we do tends to get visitors from chicken and turkey from time to time.

Top guest favourite
The exterior of the midcentury home is presented among lush greenery, featuring a brown wooden facade and small windows. Vibrant flowering plants in shades of pink and green surround the area, providing a natural frame against the serene backdrop of trees and the nearby lake.
Guest suite in West Haven
4.92 out of 5 average rating, 225 reviews

Midcentury Lakeside Guest Suite

Private guest studio suite in a beautiful, midcentury lakeside home. Built in 1957, this home on a quiet residential street is a unique piece of modern architecture around a serene lake in suburban Connecticut. It is walkable from the nearby railway station, and it is close to West Haven's picturesque beaches, and a short drive from downtown New Haven.

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