Vacation rentals in Plainfield

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Top-rated vacation rentals in Plainfield

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Top guest favorite

A serene landscape is presented, featuring expansive green fields under a softly glowing sunrise. Two rustic buildings are visible: a barn with classic doors and a white cottage, both surrounded by lush trees and open space, reflecting the peaceful countryside setting.

Guesthouse in North Stonington

4.99 out of 5 average rating, 236 reviews

"Mystic Country" Farm Stay at 100 Acre Wood

Let us welcome you to 100 Acre Wood, a historic farm and working cattle ranch. Owl's House is a private and stylish guest house nestled within the trees and garden and offers 180° views. Our farm store is stocked with our own TX Longhorn beef and pasture-raised chicken and eggs, plus curated with local products. Enjoy pastoral farm life and our private forest trails, or get out and play in the area's abundance of fine dining, wineries, seasonal attractions, outdoor activities, and entertainment.

Guest favorite

A serene view of the Poquetanuck Bay is captured at dawn, showcasing a calm water surface reflecting pastel hues of pink and purple. Surrounding trees frame the scene, while homes on the opposite shore are silhouetted against the soft morning light.

Home in Preston

4.95 out of 5 average rating, 763 reviews

Entire House Magical Waterfront Getaway

4 MINUTES TO MOHEGAN SUN! Yet quiet and secluded! Waterfront home! Come relax in this 3 bedrooms 2 baths well appointed home with breathtaking view of the Poquetanuck Bay! Enjoying the absolutely gorgeous view from the balcony or porch! Or simply relax, sit around, enjoy each other’s company! Smart TV grants you easy access to thousands of streaming apps! 25 minutes to Ocean Beach, Mystic seaport, Mystic aquariums, Submarine and Library Museum in Groton! 15 minutes away from Foxwood casino!

Top guest favorite

The exterior of a bright red caboose is captured against a backdrop of tall trees. Sunlight filters through branches, highlighting the unique structure. A pathway of gravel leads to the entrance, which features steps and a small platform. The inviting colors complement the natural surroundings.

Guesthouse in Brooklyn

5 out of 5 average rating, 56 reviews

Historic Railroad Caboose - Unique CT Farm Escape

🚂 Authentic 1906 SOO-Line Caboose on our working CT horse farm! Queen Murphy bed + two bunks, WiFi, Roku, microwave, fridge, Keurig, deck, and cozy bathroom. Note: The historic 22" doorways limit accessibility. Explore nearby: Mashamoquet Brook trails, antique shops, wineries, and Putnam's arts district. Farm life starts early! Fall asleep to railroad dreams, wake to countryside serenity. Note: historic charm means cozy dimensions. Book today—before this experience leaves the station! 🌿

Top guest favorite

The exterior view features a small wooden cabin surrounded by vibrant green trees. A stone path leads to a seating area, comprising four metal chairs and a table. Inside, the cozy octagonal space is lit by natural light filtering through several windows, showcasing a full-sized bed adorned with a colorful patterned quilt.

Tiny home in Norwich

4.99 out of 5 average rating, 936 reviews

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Top guest favorite

The exterior of the cottage is visible, featuring a blue door with a sign that reads 'THE COTTAGE.' A small deck offers a table and chairs, surrounded by colorful planters. A blue umbrella provides shade, with a scenic view of the lake and trees in the background.

Tiny home in Smithfield

4.97 out of 5 average rating, 799 reviews

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly

Good things definitely come in pet friendly, environmentally conscious, small packages. Solar upgrade makes this lake front cottage 100% energy efficient. Built with an open, thoughtful design offering private bath, washer/dryer, full kitchen, Hotel Suite Luxury bedding and Tempur-Pedic mattress, blazing fast wifi, 46"HDTV (w/ Netflix, Sling, Prime and Plex), private deck with nice lake view. Cozy, charming and stocked with everything you could want for a perfect vacation or staycation.

Guest favorite

The image showcases a spacious house nestled among trees, overlooking a calm river. The sun sets in the background, illuminating the landscape in warm tones. The surrounding area includes greenery and a small outbuilding near the house, contributing to a serene residential setting.

Home in Norwich

4.84 out of 5 average rating, 130 reviews

Hot tub with river & casino view

Looking for spacious place to unwind or crash after the casino? Our large 4 bedroom home has two en-suites and room for a group to spread out comfortably. Oh yeah were also pet friendly so bring Fido along too. Centrally located in the suburban setting we are across the river from Mohegan Sun casino just a short 5 minute drive. Foxwoods casino is only 10 minute drive. Looking for a family destination or some great dining? Just a 20 minute trip to downtown Mystic, aquarium, seaport etc.

Guest favorite

Home in Griswold

4.94 out of 5 average rating, 16 reviews

Quiet Waterfront Cottage

Enjoy a getaway at this lovely waterfront cottage. Located in a quiet neighborhood, this two bedroom home features one and a half bathrooms, home theater space, full kitchen, spacious deck overlooking the water, an outdoor picnic area and parking. Private waterfront access allows for swimming, fishing and kayaking. It's a short distance to state parks, casinos, farms, golfing, movie theater, shopping and restaurants. Enjoy day trips to Mystic CT, Rhode Island, and shoreline beaches.

Top guest favorite

A comfortable living area is furnished with a light brown sofa and two accent chairs. Artwork is displayed on the wall, and a coffee table sits atop a patterned area rug. Natural light enters through the windows, illuminating the cozy space.

Guesthouse in Killingly

4.98 out of 5 average rating, 195 reviews

The Carriage House at Chaprae Hall

Welcome to the Carriage House at Chaprae Hall! A cozy, quiet respite from a busy world awaits you. This fully furnished & appointed vintage living space has been updated over the years to be an inviting and welcoming stop for your journey. Whether you’re traveling for business, in town for an event, or looking for a central home base for day trips across southern New England, we've got you covered with your own kitchen, full bath, living space, and bedroom with a queen-sized bed.

Guest favorite

The cottage features a charming blue exterior, framed by a manicured lawn with greenery. Windows are adorned with white shutters, and a welcoming front porch is accessible via a small set of steps. Tall trees provide a natural backdrop, enhancing the serene setting.

Cottage in Chaplin

4.89 out of 5 average rating, 151 reviews

Clark Cottage in the historic village in Chaplin

Up to 14 day stays are OK. This rustic cottage, circa 1850, has antique charm, yet modern comforts. In addition to a living and dining room, there is a vintage kitchen, 2 bedrooms, 1 bathroom, laundry facilities. Very tall people will have to duck under door ways. Not suitable for children under 12. WiFi and a smart TV. Kitchen ceiling is 6'3.5". An exterior camera is installed to observe wild life passing through the yard. A switch in the laundry turns it off.

Top guest favorite

A modern kitchen features white cabinetry and granite countertops, equipped with a refrigerator, microwave, and stove. A small dining table is set with white chairs, and a potted plant adds a fresh touch. Natural light enters through a nearby window.

Guest suite in Brooklyn

4.93 out of 5 average rating, 223 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

Top guest favorite

A serene lake scene captures a modern gray house surrounded by vibrant autumn foliage. The water reflects the house and trees, creating a harmonious composition. A wooden deck is visible, leading toward the tranquil lake, enhancing the peaceful atmosphere of the setting.

Home in North Stonington

4.96 out of 5 average rating, 138 reviews

The Perch

Spring is in the air, encouraging lots of walks around the lake, visits to the local wineries and lovely walks on the beaches of Rhode Island. Nestled in the trees on a quiet lake this home is designed to be a sanctuary and a launch pad for outdoor adventures. Visit North Stonington, Stonington, Westerly and Mystic then return to your quiet spot. A short drive to store, casinos, wineries, and a walk to the forest for hikes.

Guest favorite

A spacious barn is situated in a large field, surrounded by greenery. Its two-story structure features a combination of windows and a central door, offering access to the outdoors. Lush grass and various plant life contribute to the serene rural setting.

Guesthouse in Hampton

4.95 out of 5 average rating, 169 reviews

Spacious, unique barn with beautiful views.

Our barn is in a large field on lot next to our home. Our rental area is upstairs which offers beautiful views of our field and the visiting deer. The eclectic decor is accumulated from years of activism. Our guest room and bathroom are newly renovated. It is a quiet and peaceful area near two state parks. We operate a mail order business in the downstairs area but will not be working while guests are staying with us.