Vacation rentals in Windham

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Top-rated vacation rentals in Windham

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Top guest favorite

Guest suite in Lebanon

4.96 out of 5 average rating, 135 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 favorite

The kitchen space features organized storage including wooden shelves displaying a variety of spice jars, each labeled with different colors. A wooden box is placed on a counter next to measuring tools, indicating a prepared cooking area.

Place to stay in Coventry

4.99 out of 5 average rating, 109 reviews

Get Away Rock Farm Suite UConn Best Rated Clean

The Get Away Studio Suite on Rock Farm” is a quiet, safe, airy 600 sf open floor plan with 9ft ceilings. Peaceful secluded country setting 600ft in woods. Enjoy the comfy king bed, sofa bed, kitchen, dining, living area & full bath. All Sundries & amenities. DIY breakfast on us! Near malls, shopping, lakes, 13 min UCONN, 20 min Hartford, trails & parks only mins away. WE ARE 5 ⭐️ RATED CLEAN with excellent hospitality. Need more space? See The Hide Away https://www.airbnb.com/h/atrockfarm

Guest favorite

A comfortable living area features a cozy seating arrangement with a blue sofa and an inviting armchair, set against a rustic stone fireplace. A warm light emanates from above, illuminating the wood-paneled ceiling and vibrant area rug. Large windows allow natural light to fill the space.

Cottage in Hebron

4.88 out of 5 average rating, 141 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 favorite

The exterior of a blue house is highlighted by solar panels on the roof. A stone pathway leads to the entrance, framed by lush greenery. The sky reflects vibrant colors at sunset, enhancing the overall serene ambiance of the property.

Home in Mansfield

4.81 out of 5 average rating, 47 reviews

Stunning Mansfield Getaway near UConn & ECSU

Come and see this beautiful house with so much to offer and relax with the whole family at this peaceful place to stay. House has been newly renovated with multi-zone cooling and heating systems. It has lush landscaping with a variety of trees and gorgeous lawn for privacy. The home is just 10 minutes away from UConn and has central air, deck, updated kitchen and bathroom appliances, laundry room, 2-car garage , garden beds , outdoor fire pit , shed, and gazebo, and is pet friendly!

Top guest favorite

A young piglet is seen resting on a bed of straw. Its shiny black and white fur contrasts with the golden straw, while its small ears perk up. The background features blurred earthy tones, suggesting a rustic farm environment.

Guesthouse in Portland

5 out of 5 average rating, 200 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Guest favorite

The exterior of a lakefront cottage is illuminated by warm lighting at dusk. The structure features a vaulted roof with large windows, surrounded by trees. A deck extends around the cottage, reflecting on the calm water, creating a serene and inviting atmosphere.

Home in Coventry

4.98 out of 5 average rating, 113 reviews

Cozy cottage 5 minutes from UConn

Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a warm morning coffee while enjoying the lake view from the bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

Guest favorite

A wooden sideboard with open shelving displays three wooden bowls. A single chair with a caned backrest sits nearby. Soft lighting from a standing lamp illuminates the area, highlighting the warm tones of the wooden floor and the muted wall.

Cottage in Chaplin

4.89 out of 5 average rating, 142 reviews

Clark Cottage in the historic village in Chaplin

Up to 14 day stays are OK. Cottage is empty several days between guests. Virus cleaning protocol in use. This little rustic cottage, circa 1850, has antique charm, yet modern comforts. In addition to a living and dining room, there is a full vintage kitchen, 2 bedrooms, 1 bathroom, plus 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".

Guest favorite

Home in Windham

5 out of 5 average rating, 5 reviews

4BR Willimantic House | Near ECSU, UConn & Casinos

Welcome to Thread City Escape! This beautifully updated 4-bed, 2-bath home offers 1-gig fiber WiFi, a Roku TV, a desk workspace with a monitor, and a private yard. The kitchen features a pot filler, and the living room boasts a cozy L-shaped couch. Walk to Main Street, ECSU, and Windham Hospital. Minutes to UConn & Mohegan Casino. Enjoy a stand-up tile shower and an oversized soaking tub. Perfect for families, professionals & groups!

Guest favorite

A serene view of a tranquil lake framed by lily pads and greenery, with a charming cabin visible in the distance. The still waters reflect the surrounding trees and the structure, creating a peaceful atmosphere in a natural setting.

Cabin in Windham

4.84 out of 5 average rating, 159 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!

Guest favorite

The treehouse is elevated on wooden stilts, surrounded by vibrant autumn foliage. Large windows reflect warm light, showcasing a rustic wooden exterior. A staircase leads up to the entrance, inviting guests to explore this serene retreat among the trees.

Treehouse in Willington

4.91 out of 5 average rating, 444 reviews

Treehouse - Countryside - Farm Animals - Fire Pit

Top guest favorite

A cozy living area features two light gray sofas positioned around a wooden coffee table. A mounted TV is visible on the wall, accompanied by two pieces of wall art depicting serene landscapes. A lamp provides soft lighting next to a potted plant.

Apartment in Mansfield

5 out of 5 average rating, 69 reviews

Beautiful one bedroom in convenient location

Keep it simple at this peaceful, centrally-located spot just minutes from both UCONN and Eastern Connecticut State University. Easy access to many hiking trails and Mansfield Hollow State Park. Enjoy some solitude in eastern Connecticut. Our apartment is very well cared-for and has everything a guest might need. Our house is a home, including the space you occupy.

Guest favorite

The living area features natural light streaming through large windows, illuminating a cozy seating arrangement with a striped couch. A dining table with chairs and a small wooden coffee table are included. The kitchen area is equipped with cabinets and a sink, creating a functional space.

Tiny home in Scotland

4.9 out of 5 average rating, 21 reviews

Hayfield Hideaway

Located along scenic route 14, this seasonal camper promises to provide you and yours a relaxing accommodation in the historic quiet corner of Connecticut. This seasonal camper provides all the modern amenities nestled in a rural hayfield with lots of space for you and your pet. Nearby: Wrights Mill Farm (Event Venue) Stonehurst at Hampton Valley (Event Venue)

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Popular amenities for Windham vacation rentals

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Other great vacation rentals in Windham

A view of a lake house from above is captured, showcasing a neatly landscaped yard surrounded by greenery. The stone patio is visible with outdoor furniture arranged for relaxation. In the background, the calm lake reflects the overcast sky, creating a serene atmosphere.

Home in Columbia

5 out of 5 average rating, 4 reviews

Our Little Lakehouse

CalvinRating, 5 stars2 weeks ago

Frank was wonderful and very accommodating! The place was spotless, clean, had a beautiful view of the lake, and excellent kitchen with a large table to seat several guests. There was also a very cool patio to sit with a gas fireplace for roasting marshmallows. My group included my mother and sister’s family. We ALL said we would definitely return to this AirBnb when visiting my brother’s family in Storrs. Thank you Frank for a beautiful and fantastic stay!

Top guest favorite

A modern kitchen features wooden cabinetry and granite countertops. Stainless steel appliances include a stove, microwave, and refrigerator. The kitchen island offers additional workspace and seating. Natural light is present through a nearby doorway leading to other areas of the apartment.

Apartment in Manchester

4.97 out of 5 average rating, 68 reviews

Cozy 1 bedroom clean and quiet

GailRating, 5 stars3 days ago

Megan was quick to respond and host me for a last minute reservation. Super clean space, comfortable bed and quiet location. I got a great nights rest. I didn’t make use of the full kitchen or washer & dryer but they are definitely an added bonus! Don’t hesitate to book this gem.

A variety of chickens and a rooster are seen within a fenced area. The ground is covered with straw, and a shelter is visible in the background. The birds display different colors and sizes, creating a lively atmosphere in the homestead setting.

Guesthouse in Franklin

5 out of 5 average rating, 4 reviews

Homestead Guest Quarters

IbrahimRating, 5 stars1 week ago

I had a great stay! The studio was clean, and exactly as described. It was close to everywhere I needed to go, which made things super convenient. Check-in and check-out were seamless, and the host was friendly and communicative. Would definitely stay again!

Guest favorite

A peaceful view of a lake is framed by tall trees and grassy areas. A wooden deck with seating options overlooks the water. In the distance, the shoreline is lined with a white fence and a few homes are visible along the edge of the lake.

Home in Coventry

5 out of 5 average rating, 6 reviews

Cottage on lake, 10 min to UConn

LucyRating, 5 stars1 week ago

My two daughters and I had a great stay at Gina's place for 2 nights while visiting my mother. Visiting Mom is increasingly more difficult as her Alzheimer's has progressed, so having a comfortable place to stay is critical. The girls and I were able to retreat to the little cottage to rest and relax. It was very comfortable, well-appointed, and the proximity to the lake made for lovely walks . Gina communicated with us frequently and was very friendly. We will definitely be back!

A wooden deck features two metal chairs positioned around a potted plant. Sunlight filters through surrounding trees, creating a serene atmosphere. The deck showcases natural wood tones, enhancing the outdoor experience.

Guesthouse in Brooklyn

5 out of 5 average rating, 3 reviews

Historic Railroad Caboose - Unique CT Farm Escape

JennyRating, 5 stars1 week ago

This was an amazing place to stay with my three year old! Laurie’s husband came out to show us around the place and my son grabbed his hand right away and was so excited! They had teddy bears and books set up for him and he loved every minute of it! When we woke up the next morning he said “I don’t wanna leave this place!” 10/10 recommend to anyone looking for a cozy getaway!

Top guest favorite

A spacious kitchen is presented with a large granite island, offering ample seating. Custom cabinetry in pale hues complements the bright yellow walls. Natural light streams through large windows, illuminating the area and highlighting decorative plants in the adjoining space.

Private room in Mansfield

5 out of 5 average rating, 100 reviews

Woods Room

LeslieRating, 5 stars4 days ago

Terry and Judy are amazing hosts. They are gracious and friendly but give you space to enjoy being on your schedule in their home. I loved the trees all around, the quiet, joyfully painted room and all the light. The whole house is beautifully painted and so very clean! They provide everything you could need and more. I ended up having breakfast in the kitchen with Judy and an art tour from the two hosts. They have a spectacular collection of art and stories from their adventurous life, which they will share on request. It's a wonderful place to stay.

A small cottage is situated among greenery, featuring blue siding and a white door framed by a decorative window. A stone chimney extends from the roof, while a large rock and a wooden fence separate the cottage from the surrounding yard.

Cottage in Coventry

4.73 out of 5 average rating, 37 reviews

Small cottage with view of Coventry lake!

JocelynRating, 5 stars2 weeks ago

This cottage is placed in such a beautiful area. It was so quiet and so peaceful during the day and night. It was the perfect size not too small, not too big and it was pretty easy to find. I would definitely stay here again.

The interior of the camper is showcased, featuring an organized kitchen counter with a coffee maker and a small plant. A cozy lounge area with seating and a table is visible, with natural light coming through the window.

Camper/RV in Tolland

4.58 out of 5 average rating, 12 reviews

Riverfront Glamping

StevenRating, 5 stars3 days ago

Great Place to space your mind. Love it , definitely recommended.

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Vacation rentals in Windham

Top-rated vacation rentals in Windham

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