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Places to stay in Plainville

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Top-rated places to stay in Plainville

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Barn in Deep River

4.91 out of 5 average rating, 32 reviews

Zen retreat

You won’t forget your time in this romantic, memorable place. Perfect for a couple that want to retreat to renew and reset. Bathroom has an accujet shower in a steam capsule. Outdoor shower and bath tub in our healing garden. Swimming pool (in season) with a sun deck. Meditation garden and weeping willow will relax and rejuvenate your spirit. Wintertime a sauna is available after we close the pool. Windows and some of the furnishings were last in Katherine Hepburns home. Imagine the stories.

Apartment in Chester

4.99 out of 5 average rating, 89 reviews

The Millhouse Downtown Chester

An upscale destination with accommodations for foodies & friends in the heart of historic Chester CT. Stay at this beautifully renovated historic Millhouse in charming downtown Chester. Enjoy strolling the streets loaded with shops, award winning restaurants, a microbrewery, art galleries, and more. All within a 1 minute walk. Our prime location is just 20 minutes to the CT shoreline and located in the heart of the CT River Valley. The Millhouse is next door to the Chester Historical Museum.

Home in Roxbury

5 out of 5 average rating, 10 reviews

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

Vacation home in Torrington

4.95 out of 5 average rating, 189 reviews

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.

Home in Sheffield

4.9 out of 5 average rating, 115 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Guesthouse in Bethel

5 out of 5 average rating, 13 reviews

Tranquil getaway cottage in charming neighborhood

Escape the city bustle and unwind in the tranquility of The Red Cedar Cottage nestled between Bethel and Newtown, just a short drive from Danbury, CT. Tucked away in a peaceful neighborhood, this fully renovated cottage offers a serene getaway for couples seeking relaxation. Unwind in style on a high-end king-sized mattress in a whimsically curated space designed to rejuvenate your senses. Discover the Red Cedar Cottage and immerse yourself in a tranquil escape from the ordinary.

4.99 out of 5 average rating, 103 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 yearround!

Home in Westville

4.97 out of 5 average rating, 38 reviews

7 Mins drive to Yale | Large fenced yard

Nestled in the charming neighborhood of New Haven, our home offers the perfect blend of tranquility and convenience. You'll enjoy a peaceful retreat surrounded by tree-lined streets, all while being just a stone's throw away from the vibrant energy of Yale University and the cultural richness of New Haven. Explore local parks, dine at renowned restaurants, and discover the city's unique character, all from your cozy home base in New Haven.

Home in New Milford

4.97 out of 5 average rating, 29 reviews

Serene Country home 24 mi Mohawk ski area

THIS IS A PRIVATE HOME🏡 THE BOTTOM FLR 2 car garage and a double bedroom with a full bathroom attached. THE MIDDLE FLR KITCHEN, LIVING, DINING 1/2 bath, wrap-around decks w/ a fire pit THE TOP FLR 1 K rm w/ a fireplace & a private deck 1 Q rm 1 ba w/ jet tub & standing shower 6 acres Foothills of the Berkshires May-Sept We provide day passes for access to tennis, pickle ball, pool, yoga, swim, water aerobics

Chalet in Litchfield

5 out of 5 average rating, 21 reviews

SerenityCT

New! Litchfield, Connecticut Nestled on 7 acres in the heart of a charming, quintessential New England town, our Chalet styled home offers a unique vacation rental. Enjoy the feel of nature without sacrificing the luxury of comfort. Experience rich history, nearby vineyards, hiking trails, breweries, nature and so much more!

Apartment in Downtown New Haven

4.84 out of 5 average rating, 345 reviews

A Cut Above

Upscale studio. Private entrance. Queen bed. Tile bathroom. You are provided with a refrigerator, microwave, toaster oven, and a hot water kettle. Ample closet space. Desk area. Recliner and TV. Light and airy. Free off-street parking nearby by request. Backyard Seating. Umbrella - in case you forgot yours.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Plainville places to stay

Laptop-friendly workspace

Air conditioning

Stay near Plainville's top sights

Lake Compounce72 locals recommend

99 Restaurants6 locals recommend

AMC 20 Plainville6 locals recommend

ESPN Headquarters5 locals recommend

J Timothy's Taverne5 locals recommend

Hidden Valley Miniature Golf4 locals recommend

Other great vacation rentals in Plainville

Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

5 out of 5 average rating, 13 reviews

The Mountain Vacation Home

Cottage in Guilford

4.99 out of 5 average rating, 130 reviews

"Red House on the Knoll" at Indian Cove

Bungalow in Old Lyme

4.94 out of 5 average rating, 295 reviews

Pet Friendly Bungalow!!!

Home in Cornwall

4.82 out of 5 average rating, 93 reviews

State Forest Getaway

Home in Woodmont

4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

Home in Old Saybrook

5 out of 5 average rating, 44 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

Guest suite in Branford

4.9 out of 5 average rating, 100 reviews

Granite Bay Getaway - Private Studio Apartment

Quick stats about vacation rentals in Plainville

Total rentals
20 properties
Nightly prices starting at
G$6,267 GYD before taxes and fees
Total number of reviews
1K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Frequently Asked Questions

How much does it cost to stay in apartment rentals in Plainville?
Experience the best of Plainville with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for Apartment Rentals in Plainville?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Plainville?
Yes! Work meets play with ease at over 10 vacation rentals in Plainville featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Plainville have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Plainville. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Plainville have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Plainville. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Plainville have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Plainville. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore