
Holiday houses in Plymouth
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Top-rated holiday rentals in Plymouth
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away
Discover a charming 1080 sqft lakefront cottage offering modern comfort and tranquility. Wake up to peaceful Lake Garda waterfront views while staying near Farmington Valley’s conveniences. This newly remodeled retreat features a large jetted swim spa, stone patio with fire pit and grill, and direct lake access for kayaking or pedal boating perfect for relaxation. Enjoy a private getaway with nature’s beauty at your doorstep, all while being minutes from dining, shopping, and outdoor adventures.

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.

Cozy escape w/private hot tub & backyard skatepark
Relax and make some memories with your family and/or friends at this peaceful and cozy place to stay. This four bedroom house is comfy and unique. It has everything you need to make your stay comfortable and fun for all! We are located in a quiet wooded area with a spacious yard in close proximity to restaurants, grocery stores, and most amenities. Whether you’re relaxing on the patio, soaking in the hot tub or rolling around the concrete backyard skatepark it will be a memorable stay!

Cozy Oasis, Lakefront with Stunning Sunset Views
It’s the Lakefront Paradise you’ve been searching for: Escape to Cozy Oasis where peaceful waters meet modern comfort! Wake to stunning views, spend the day kayaking around the lake, and unwind with breathtaking sunsets from your private deck. This pet-friendly retreat offers high-speed WiFi for remote work, fully equipped kitchen for home-cooked meals, and cozy entertainment spaces. Perfect for romantic getaways or family adventures - your serene lakeside escape awaits! Pet friendly!

Charming 3BR Hill House *Remodeled* w/Arcade
The Lindan Hill House is a perfect AirBnb balance of luxury and value! Stay and play as you enjoy our 5 Star remodeled charming home in Terryville. This quaint and comfy home has everything you need to enjoy your stay including 3 BR with a King/Queen/2 Twin beds with premium bedding. The cozy remodeled basement is perfect for popcorn and movies, dinner and drinks at the bar, and has a game/arcade room with foosball, checkers/chess, and tons of board games! See below for a video tour.

The Cottage on Babbling Brook
A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

The Farmhouse
Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Artist's Garden Apartment
Private second floor apartment with entrance. Detached from the host's main house. Overlooks perennial herb and flower gardens located in the backyard. Walking distance to White Memorial Nature Preserve and the historic Litchfield Center. Walk or bike from the backyard to shopping, restaurants, art galleries, bakeries, or to a 3000 acre nature preserve and take in the Flora and Fauna. Quiet residential neighborhood that is close to so many amenities and activities.

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes
This vintage style cottage offers guests a comfortable and convenient stay in Litchfield with it’s range of amenities. Essential amenities include air conditioning, cooking basics, a dedicated workspace, dishes and silverware, a dryer, hair dryer, heating, hot tub, kitchen, TV, washer, and Wi-Fi. 5 Min - Litchfield Town center 9 Min - Arethusa Dairy farm- Restaurant 10 Min - White Memorial Conservation Center 8 Min - Bantam Lake 19 Min - Mohawk Mountain Ski Area

Cozy Family Home - Kid & Pet Friendly
3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Spacious Cozy Guest Suite
This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.
Popular amenities for Plymouth holiday rentals
Other great holiday rentals in Plymouth

Charming Lakefront Retreat with Spring Lake Views

Modern Ranch style apartment.

Cozy Cabin By The Brook One

Lakefront Retreat | Hot Tub + Summer Fun

Lakefront Getaway • Hot Tub, Decks, Fires & More

Private studio guesthouse

Carriage House on Smith Pond!

Secret Mountain Cabin/Catskills Views/100-Acres
Destinations to explore
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- Yale University
- Six Flags New England
- Fairfield Beach
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Taconic State Park
- Kent Falls State Park
- University of Connecticut
- Hammonasset Beach State Park
- Mohawk Mountain Ski Area
- Compo Beach
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Yale University Art Gallery
- Ski Sundown
- Sherwood Island State Park
- Millbrook Vineyards & Winery
- Soundview Beach
- Wesleyan University
- Benmarl Winery
- Norman Rockwell Museum
- Mount Southington Ski Area





