Holiday rentals in Plainfield

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Top-rated holiday rentals in Plainfield

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

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Top guest favourite
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.
Guest house in Brooklyn
5 out of 5 average rating, 63 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! 🌿

Guest favourite
Flat in Windham County
4.93 out of 5 average rating, 55 reviews

Bunny’s 15-Acre Woodland Retreat

With 15 acres of private wooded land, count on High Speed Wi-Fi throughout Bunny's Retreat if you work from home or just need to catch up on emails! Coffee bar is stocked, have a cup taking in an ideal view of the woods! Television is ready to stream movies with family & friends! Plenty of indoor & outdoor seating for meals as you watch the sunrise or sunset cast pink hues over the woods & sky! As the sky darkens & the stars light up, gaze up in wonder in a very quiet area of New England!

Top guest favourite
Home in Griswold
4.95 out of 5 average rating, 19 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 favourite
The exterior of a spacious barn structure is visible against a clear blue sky. The building features a gabled roof and light-colored wooden siding. Large double doors are positioned at the front, with a smaller door on the side. Leafless trees surround the barn.
Barn in Hampton
5 out of 5 average rating, 58 reviews

Little Rest Studio

Little Rest Studio overlooks 100 acres of conservation land, primarily oak and hickory forest. Recently renovated by the owners and full of personal, handmade touches, this apartment was originally conceived as a temporary ARTIST’S residence and occupies the top story of an English-style BARN otherwise used as a photographer's WORKSHOP. We offer a chance to slow down and meet the season, relax in the warmth of the wood stove or the bath, and be a human in a lovingly handmade retreat.

Top guest favourite
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.
Guest house in Killingly
4.98 out of 5 average rating, 197 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.

Top guest favourite
Cabin in North Stonington
5 out of 5 average rating, 14 reviews

Lakeside Landing

Welcome to our serene lakeside getaway! Central to all area attractions, yet an oasis of calm. Minutes from vineyards, museums, beaches, restaurants, casinos, and everything Mystic Coast & Country offers!! Note: this is a rural space with all kinds of wildlife in evidence. We know you will love our perfect lakefront getaway, a little gem that will leave you relaxed for your area adventures. Unfortunately no pets: an automatic $500 charge if pets brought onto property.

Top guest favourite
The exterior of a red, two-story building is surrounded by a well-maintained lawn featuring trees and landscaped flower beds. A large window above the entrance and additional windows enhance the farmhouse aesthetic. Cloudy skies and natural light create a serene atmosphere.
Farm stay in Woodstock
4.99 out of 5 average rating, 225 reviews

Barn suite at Southwood Alpacas

Country living at its best. Renovated guest space on a working alpaca farm. This is a two story unit with a kitchenette, living room and bathroom on the first floor and a studio loft on the second floor. Two decks, one on each level overlook the farm. Recently renovated. Great light floods the unit. Central heat & AC. Enjoy the farm and the bucolic setting in Woodstock. Watch the alpaca from your windows or deck. Cafes for morning breakfast and fine dining await.

Top guest favourite
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, 227 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.

Guest favourite
An aerial view captures a charming ranch home surrounded by greenery. The building features a warm red exterior and a stone chimney. Flowering shrubs and trees enhance the inviting landscape, while a stone pathway leads to the front door, inviting guests to explore the property.
Home in Brooklyn
4.89 out of 5 average rating, 28 reviews

Brooklyn Bear’s Den

Charming 2-Bedroom Ranch Retreat on 3 Acres Escape to tranquility at this cozy 2-bedroom, 1.5-bath ranch on a private 3-acre lot. Enjoy a lush backyard oasis surrounded by rhododendrons and nature's sounds, perfect for unwinding. Conveniently located near local shopping, and dining with easy access to Rt 169, Rt 6, and Rt 395. Spacious living make this the ideal peaceful retreat. Book your stay for a memorable escape!

Guest favourite
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.
Guest house in Hampton
4.95 out of 5 average rating, 171 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.

Guest favourite
The image shows a spacious farmhouse nestled among trees, featuring a porch with multiple steps leading to the entrance. A gravel driveway is lined with a wooden railing and a fenced area, while a garage structure is visible in the background.
Home in Coventry
4.94 out of 5 average rating, 71 reviews

painted acres country getaway

Forget your worries in this spacious and serene home on 5.8 acres. Whether you are looking for a quiet place to work, re-charge, or just get away, this newly renovated farm house is a great place to do it. Everything inside has been updated, from a whole newly outfitted kitchen to new bathrooms. Outside there is a fire pit flanked by ponds and an outdoor kitchen. Pets are allowed with permission and a $50 fee

Top guest favourite
A spacious kitchen area features modern appliances and a central island with seating. Light-colored cabinetry complements the dark flooring. Sunlight enters through a window, illuminating a neutral color palette, while an adjacent living area is subtly visible in the background.
Flat in Plainfield
4.99 out of 5 average rating, 78 reviews

2 Bd Apt- 20 min to Foxwoods/25 min to Mohegan Sun

Very new, clean and quiet 1000 sqft 2 bedroom apartment. The apartment is located over an office and is 20 minutes from Foxwoods and 25 minutes to Mohegan Sun. You’ll have the whole apartment to yourself with access to central AC, thermostat controls heat, WiFi and laundry - much better than staying in a hotel! Bedroom 1: Queen sized mattress Bedroom 2: Queen sized pull out sofa.

Popular amenities for Plainfield holiday rentals