Vacation rentals in Windham

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Top-rated vacation rentals in Windham

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Top guest favourite
A vibrant sunrise casts shades of orange and pink across the sky, illuminating the expansive green fields. A white fence lines the foreground, while horses are visible grazing in the distance against a backdrop of tree-covered hills.
Guest suite in Lebanon
4.96 out of 5 average rating, 145 reviews

Rural Homestead Stay in Your a Private Suite

Relaxing country setting secluded off a long private driveway, on a dead end road, in historic Lebanon, Connecticut. Horses line the driveway, and chickens roam the yard. Sunrises over the backyard amongst the tree covered hills. The private accessory apartment, attached to the main home, includes one bedroom, living area, kitchen, bathroom, & porch. Witness the bustle of the active homestead. Relatively close to landmark casinos (Foxwoods & Mohegan Sun), hiking, the shoreline & historic sites.

Top guest favourite
A spacious living area is characterized by high beamed ceilings and large windows that allow natural light. Furnishings include a round dining table surrounded by six chairs and a comfortable seating arrangement, featuring a decorative rug. A large television is positioned on a wooden stand.
Apartment in Coventry
5 out of 5 average rating, 132 reviews

HideAway UConn Coventry RockFarm BnB Breakfast A+

Enjoy your visit at “The Hide Away” on RockFarm with Super Hosts Jon & Jeri. The family friendly private 1000+ sf 2 bdrm apt wooded, well lit, all amenities of home. WIFI 500 Mbps, TV ROKU. Enjoy the private deck, kitchen, laundry, lvg rm & Dining. DIY Breakfast. UConn 15 min, Bolton Lakes 2 min fishing & hiking trails. View our VIP GUEST BOOK for activities & good eats! No-shoe, clean, comfy secluded BnB. 5⭐️ 100% loved! 32 yrs no crime! See the Get Away too. https://www.airbnb.com/h/onrockfarm

Top guest favourite
A charming cottage features wood shingle siding and a neatly arranged entrance. The front yard showcases a manicured area with green grass, accompanied by a duck and a chicken. Nearby, expansive fields and a rustic barn complete the serene rural landscape.
Guesthouse in Portland
4.98 out of 5 average rating, 286 reviews

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Top guest favourite
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 homes in Norwich
4.99 out of 5 average rating, 915 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 favourite
A spacious living area is furnished with a gray sectional sofa, accented with colorful throw pillows. A wooden coffee table is placed in front, on a soft area rug. Two large windows allow natural light to brighten the room, complemented by ceiling fans and tasteful decor.
Loft in Tolland
4.96 out of 5 average rating, 311 reviews

Cozy studio loft

Home away from home! In a serene, wooded area tucked away from the road, you'll find our studio loft mother-in-law apartment. Beautiful views with wildlife often spotted. Well-lit with many windows to let in the morning light. Suitable for a change of scenery while working remotely, a brief stay between locations, or your actual destination. UConn is minutes down the road. Looking for antiques? Stafford Speedway? Mohegan Sun or Foxwoods visits? Outdoor enthusiast? This place works for all!

Top guest favourite
A bright bedroom features a queen size bed with light linens and decorative pillows. A small desk and chair are positioned beside the bed. A closet offers hanging space, and a floral artwork adorns the wall, adding a touch of color to the space.
Guest suite in Vernon
4.98 out of 5 average rating, 213 reviews

Laura's Loft and Gallery, private suite

Unique and spacious loft with private entrance, two bedrooms with space to sleep 5, full bath with tub shower, and plenty of room to relax. Kitchen with mini fridge, toaster oven, microwave, hot plate. Pleasant living area opening to 2nd floor deck. WiFi with Ethernet also, great remote work space. Quiet and private, only common area shared with us is first floor entry into breezeway. Free parking on premises. Full coffee setup, plus homemade scones in seasonal flavors for your enjoyment!

Guest favourite
A charming two-bedroom cottage is set amidst greenery, featuring a welcoming front porch with a railing. A stone pathway leads to the entrance, and landscaping is visible around the base of the home. Large windows allow natural light to enhance the inviting exterior.
Cottage in Hebron
4.89 out of 5 average rating, 170 reviews

Welcome to The Holly at Amston Lake

Welcome to The Holly at Amston Lake! Great two-bedroom cottage situated in a peaceful lake community. Great place to enjoy time with family and friends. Take a stroll down to the main beach or enjoy the great views of the lake from the deck! Don't forget about the gas fire pit for those chilly evenings. We are located near numerous vineyards, a brewery, the Connecticut Airline Trail, and great local restaurants! Guests have access to the grill, fire pit, kayaks, and two main beaches.

Guest favourite
A serene bedroom features a spacious bed adorned with white bedding and decorative pillows. Nightstands with lamps flank the bed, and a cozy couch with patterned cushions offers additional seating. Natural light filters through sheer curtains, enhancing the calming environment.
Condo in Norwich
4.91 out of 5 average rating, 224 reviews

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf

Spa Resort | Casinos | Heated Seasonal Pool and Hot Tub | Sauna | Fitness Room | Clubhouse | Golf | Restaurants | Heated Massage Chair | Warm Robes and Blankets | Electric Fireplace with Remote| New Serra topper Whether you’re looking to get away or jump in, enjoy this relaxing retreat surrounded by upscale amenities! We’ve done our very best to ensure your stay is comfortable and tranquil, full of necessities and extras, and that there are many nearby options for adventure and fun.

Guest favourite
The living room showcases a comfortable seating area with a dark couch, complemented by a glass dining table nearby. A wooden mantel above a decorative fireplace adds warmth, while natural light filters through the large windows, illuminating the soft white walls.
Apartment in Ashford
4.97 out of 5 average rating, 270 reviews

Enjoy a Farm Stay without the Work

This 3-room one-story apartment with private entrance is attached to the main 1850 farmhouse and also has that older farm charm. Only 10 minutes to Interstate 84 and midway between New York City and Boston, this location allows for ease of access to experiences in the northeast. The property is set back from the state road (Route 89) and allows for relaxed living on a beautiful farm bordered by stone walls and wooded area behind.

Superhost
A gravel area is surrounded by trees, featuring a fire pit and multiple plastic chairs in various colors. A picnic table sits at the center, with a scenic view of a pond visible in the background. A swing set is positioned nearby under the trees.
Cabin in Windham
4.83 out of 5 average rating, 186 reviews

Secluded Cabin on Golden Pond

• Cozy Cabin on Golden Pond! • Fire Pit, (free wood)! • Fishing! • Kayak, Paddle Boat Canoe, Row boat! • Hiking! • Swimming! • Sand Beach! • Picnic Table, Chairs! • Grill! • WiFi! • Cooking Utensils, Service 4 six! • Air Conditioning! . Soap Stone Fire Place! . Comfy Couch, Smart T.V.! . Beds: 2 Full, 2 Twin, 1 Queen on Porch! • 14x14 Tent platform at waters edge! (Camping gear not provided) • Secluded! • Wildlife!

Top guest favourite
A spiral staircase with a sleek black railing leads to the loft bedroom. A mirror with a burgundy frame is mounted against the wall, reflecting the light. The open living area features a light-colored couch and a wooden dining table, visible through large windows offering views of the outdoors.
Guesthouse in Mystic
4.98 out of 5 average rating, 670 reviews

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Top guest favourite
Guest suite in Mansfield
4.96 out of 5 average rating, 224 reviews

Cozy private apt 8 mins from UCONN - solar powered

Relax & unwind in this amply sized private studio suite, complete with large seating/tv area & study/desk space. Space comes w/ 2 beds (1 queen, 1 full sized pull out futon couch) a full private bath, mini-fridge, cooktop, microwave, dishware, & utensils. Beautiful rural wooded area with numerous hiking trails nearby. Longer term rentals may be considered starting from Summer of 2025

Popular amenities for Windham vacation rentals