Vacation rentals in Plymouth

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Top-rated vacation rentals in Plymouth

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

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Top guest favorite
A spacious deck features a traditional wood-burning hot tub, reflecting the surrounding trees and sky. Nearby, a dining set provides a place to enjoy meals outdoors, surrounded by the natural beauty and serenity of the cabin's setting.
Cabin in New Milford
5 out of 5 average rating, 107 reviews

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub

Step into the stylish and peaceful 3BR 2.5BA cabin in a historic Merryall District close to shops, lakes, hiking trails, farms, and downtown New Milford and Kent. Explore the picturesque area and the exciting attractions, or lounge by the fireplace or the fire pit in the magical yard. ✔ 3 Comfortable Bedrooms ✔ Living Room & Sunroom ✔ Wood Burning Hot Tub ✔ Chef's Kitchen ✔ Office/Library ✔ Books, Vinyls & Games ✔ Porch, Yard & Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry See more below!

Top guest favorite
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.
Guesthouse in Watertown
4.94 out of 5 average rating, 114 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.

Top guest favorite
Home in Plymouth
4.99 out of 5 average rating, 116 reviews

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!

Top guest favorite
Cottage in Bethlehem
4.99 out of 5 average rating, 158 reviews

Cozy Cottage |Quintessential CT | Pet Friendly

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

Top guest favorite
A wooden dock extends over calm lake waters, framed by vibrant hues of pink and purple in the sunset sky. Two adirondack chairs are positioned on the dock, inviting relaxation while enjoying the serene views, with softly glowing lanterns along the water's edge.
Cottage in Plymouth
4.94 out of 5 average rating, 144 reviews

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!

Guest favorite
Home in Plymouth
4.96 out of 5 average rating, 135 reviews

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.

Guest favorite
Cottage in New Milford
4.95 out of 5 average rating, 241 reviews

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.

Guest favorite
The cabin is nestled among green trees, with a dark exterior blending into the natural surroundings. Large windows illuminate the interior, providing a glimpse of the inviting living space within. The vibrant foliage and lush undergrowth create a serene and secluded atmosphere.
Cabin in Sherman
4.96 out of 5 average rating, 440 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Guest favorite
Tiny home in New Marlborough
4.94 out of 5 average rating, 168 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Top guest favorite
A charming house is visible along the riverbank, surrounded by lush greenery and blooming trees. The landscape features the calm waters of the river, reflecting the clear blue sky dotted with soft clouds, providing a scenic backdrop to the quaint property.
Home in Canton
4.99 out of 5 average rating, 131 reviews

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

Top guest favorite
Cottage in Pawling
4.99 out of 5 average rating, 171 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Top guest favorite
Apartment in New Britain
4.96 out of 5 average rating, 268 reviews

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 vacation rentals