
Vacation rentals in Windham
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Top-rated vacation rentals in Windham
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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.

Getaway on RockFarm, UConn Quiet Retreat in Woods
The Getaway on Rock Farm, a quiet retreat designed for slow mornings, golden hours & deeply restful nights. A 600sf King Studio suite guests love. Option for an adult twin or add 1-2 children on the sofa bed. A living room, kitchen (DIY breakfast), dining & bath w/sundries & amenities. Great connections, WIFI 500 Mbps & ROKU TV. Play yard, outdoor dining, parking. A clean Suite w/superlative hospitality. The Getaway on Rock Farm is for people who don’t want more — they want less, done well.

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.

Charming Cottage by the Lake
Come stay at our CHARMING COTTAGE💗 in Coventry Lake 🚣🏝️ PRIVATE BEACH for members and guests only! ⛱️ Relax on this quiet dead-end road in a quaint community.🌳 Our property has a huge yard with a DOG RUN 🐶, Large FIRE PIT 🔥, GAS GRILL 🥩, SWING SET and TREEHOUSE for kids, and off-street parking! - 2 COMPLIMENTARY kayaks available to use while you are our guests. ⛵ -Queen bed 🛏️ -Full bed 🛏️ -2 Twin Beds 🛏️ Walk to Popular Coventry Farmers Market! 🍏 10 Mins to UCONN

One bedroom newly renovated clean and quiet. Apt F
Your home away from home. Queen size bed. End unit facing the woods in a quiet 6 unit apartment building. Off street parking. Pay laundry. Food shopping only a 2 minute walk for that emergency ice cream fix or last minute beverage. 5 minute drive to romantic Willimantic and 15 to Norwich. Casinos are 25 minutes away. All appliances are brand new as of 1/20/21. Glass top stove, fridge, microwave and dishwasher. Tile wood and carpet are also new and has central heat and air conditioning.

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!

Windham Gardens
Our guesthouse is a newly-renovated bespoke cottage located on the grounds of the circa 1750 Windham Gardens estate in the heart of historic colonial Windham Center. The cottage sits in the midst of a private garden, with several intimate outdoor seating areas. The cottage has a bedroom, bathroom, and a orchid filled garden conservatory with a retro kitchenette. The garden cottage is just 15 minutes from UConn and close to numerous restaurants and antique shops.

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.

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.

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

The Carriage House
Nestled in the woods, this secluded lower guest suite offers everything you will need for a relaxing stay. A very easy 20 minutes to Hartford or a quick 15 to UCONN. Private, full kitchen, bathroom, and laundry. Free level 2 EV car charging. Tons of space, a sunny deck and private entry. Ideal for a quick weekend or an extended stay.

Eco-Friendly Garden Studio
Kick back and relax in this calm, stylish space, surrounded by gardens with large windows for viewing flowers or snow. Solar panels and a mini split heat pump make it ecological. There is a fully equipped kitchen, a patio and a separate entrance from the main house.
Popular amenities for Windham vacation rentals
Stay near Windham's top sights
Other great vacation rentals in Windham

The Red Room
Sunny Bedroom in Cozy Bungalow

Lakeside Willow

Glastonbury Center off Main St!

Safe Suburban Neighborhood 20s/30s

Finished carpeted basement with private bathroom.

Secluded colonial in an idyllic country setting

Woods Room
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- Yale University
- Foxwoods Resort Casino
- Brown University
- Charlestown Beach
- Six Flags New England
- Ocean Beach Park
- Easton Beach
- Roger Williams Park Zoo
- Mohegan Sun
- Second Beach
- East Matunuck State Beach
- Bonnet Shores Beach
- The Breakers
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Mystic Seaport Museum
- Mount Southington Ski Area
- Yale University Art Gallery
- Burlingame State Park
- Sleeping Giant State Park
- Fort Adams State Park
- Ski Sundown
- Salty Brine State Beach
- Orient Beach State Park




