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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Guest favorite

Apartment in Bristol

4.96 out of 5 average rating, 25 reviews

1br-queen-0cleanFee-w/d-offstreet park-NursesNest

Step into tranquility in this charming 1 BR, 3rd floor retreat, affectionately referred to as Nurses Nest, an ideal haven crafted for the discerning working prof. This cozy apt offers the perfect blend of comfort and sophistication. Fully-equip kit., complete with modern appliances. The dining area offers a tranquil spot within this retreat, setting the tone for a calm and centered day. Ample closet space, full size W/D and a thoughtfully designed layout, seamlessly combine functionality w/style

Top guest favorite

Guest suite in Watertown

5 out of 5 average rating, 76 reviews

Private King suite w/ separate entry-Walk to Taft!

Enjoy Litchfield County, CT! This renovated 1-bedroom guest suite in an 1859 historic home has a private entrance off a dedicated covered porch. Enter through the private stairway into the bedroom with a King size bed and comfortable foam mattress. French doors open into a living room with a pullout full size sofa bed and a Nespresso coffee maker. The renovated bath has marble floors and a glass door shower. Free parking for up to two cars in the drive and directly across the street from Taft.

Top guest favorite

Guesthouse in Litchfield

5 out of 5 average rating, 13 reviews

The Jefferson Guest House, Spacious, Special Views

Bask in this tranquil estate. Exceptional views, the sunrises are world class, many have said "the sky speaks to you here." 95 Acre Estate and gentlemen's Farm with a guest house for you to explore and enjoy Litchfield, NW CT & The Berkshires. Sleeps 4, complete apartment with a king bed, queen sleeper sofa, wifi, washer/dryer, sound bar, coffee bar. Apple orchard, hay fields, chickens, 8 miles of walking trails to explore. Couple of homes away from Topsmead Park. Exceptional & Private.

Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 200 reviews

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

Top guest favorite

Guest suite in Bethlehem

4.99 out of 5 average rating, 312 reviews

Quiet cottage w/chickens, gardens near Litchfield

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and summer fun!

Guest favorite

Guesthouse in Watertown

4.92 out of 5 average rating, 52 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 Terryville

4.98 out of 5 average rating, 53 reviews

Cozy New England Escape! Hot tub & 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 spacious 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 jacuzzi or rolling around the concrete backyard skatepark it will be a memorable stay!

Top guest favorite

Guest suite in Bloomfield

4.94 out of 5 average rating, 102 reviews

Private Cozy Suite, 0 Fees, Easy CheckIn, EV Plug

A private cozy suite for you! Better than a hotel or private room & less than an entire house. We do not charge extra fees! Big discounts for medium- to long-term stays. Your guest suite includes a living room, kitchenette, bedroom & FULL bathroom. Your heating, cooling and hot water are all-electric. Despite many renovations, we kept the vintage & cozy theme. Separate Wifi for remote work. Less than 20 minutes to the airport, downtown and the Hartford metro; golf and state parks nearby!

Top guest favorite

Guest suite in Plymouth

4.94 out of 5 average rating, 63 reviews

Secluded | Cozy | Nature

Located at the end of the cul de sac, access the Calathea guest suite by driving down the beautiful 300-ft pea stone driveway. The property sits on 2 acres surrounded by 200 year-old oak trees and greenery. You’ll find calming views as you follow the steps down to the private entrance of your stay. Plymouth is a quiet farm town located in Litchfield County, approximately 2 hrs from NYC or Boston. It’s perfect for couples, solo travelers, outdoor enthusiasts, and traveling/remote workers.

Guest favorite

Home in Terryville

4.96 out of 5 average rating, 117 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 Plymouth

4.94 out of 5 average rating, 126 reviews

Lakefront Cozy Oasis 2BR w/ 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!

Guest favorite

Home in Bristol

4.93 out of 5 average rating, 187 reviews

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.