Holiday rentals in East Windsor

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Top-rated holiday rentals in East Windsor

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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.
Flat in Coventry
5 out of 5 average rating, 143 reviews

HideAway UConn Coventry RockFarm BnB Breakfast A+

Welcome to “The Hide Away” on Rock Farm with Superhosts Jon & Jeri. A private, family-friendly 1000+ sq ft wooded retreat featuring two bedrooms, 500 Mbps WiFi, Roku TV, private deck, full kitchen, laundry, and DIY breakfast. Just 15 minutes to UConn and 2 minutes to Bolton Lakes for fishing and hiking. See our VIP Guest Book for local favorites. Clean, cozy, no-shoe secluded BnB — 5⭐️ guest favorite. Ask about “The GetAway” too! It’s our King Studio Suite, a private space, perfect for couples.

Top guest favourite
A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.
Chalet in Otis
4.95 out of 5 average rating, 465 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Superhost
A globe rests on a polished surface, accompanied by a wooden 'Hello!' sign. Sheer curtains filter soft light, creating a bright and welcoming scene. The composition offers a blend of decorative elements that enhance the living space.
Home in South Windsor
4.88 out of 5 average rating, 173 reviews

Spacious 3 Bedroom Ranch With Office

Forget your worries in this spacious and serene space with room for 8. The entire first floor is yours to enjoy and there aren’t any shared spaces. Relax in the backyard or on the porch. 2 full bathrooms are yours to relax and enjoy. There’s a freshly remodeled bathroom in the master bedroom with walk in shower and a bathtub in the 2nd bathroom. Fully stocked kitchen awaits your inspiration. Much shopping awaits you and all the store are within 10 minutes away from you. BDL is 20 minutes away,

Superhost
A bright workspace features a wooden desk with a black chair, positioned against a light-colored wall. Two framed botanical prints are displayed above the desk, complemented by a standing lamp. A mirror reflects the scene, while a potted plant adds a touch of greenery.
Flat in Windsor Locks
4.83 out of 5 average rating, 192 reviews

Apt near Big E, Six Flags, Bradley airport

Welcome to our charming and stylish upstairs apartment, perfect for a cozy retreat! Enjoy the privacy of having the entire space to yourself. Access the apartment directly through the back entrance, up the outdoor staircase. We're conveniently located just a 10-minute drive from Bradley International Airport. Inside, you'll find: - A comfortable bedroom with a Queen-sized bed, complete with fresh linens - A fully stocked kitchen, equipped: Pots, pans, baking dishes, etc Washer and dryer

Top guest favourite
A cozy living room features a stone fireplace surrounded by purple walls. A wooden table sits at the center, adorned with a decorative bowl. A comfortable sofa and a wooden chair are positioned near the fireplace, complementing the warm ambiance.
Cottage in Windsor
4.9 out of 5 average rating, 204 reviews

In-law apartment in Farmington River Cottage

If you are craving a getaway with a special someone, this space is meticulously clean and an opportunity to practice social distancing while relaxing and enjoying the Farmington River. Only 15 minutes from Bradley airport, 5 minutes from the train and I91. Nature, dining, all within a comfortable drive. You get it all here! Private space with its own entrance, one bedroom and newly updated bathroom, a cozy living room with fireplace in a Garden Level Unit. Off street parking available.

Guest favourite
A cozy studio space features a spacious bed with a light coverlet and decorative pillows. A neutral rug lies beneath, complementing the wooden flooring. Decorative wall art and plants are displayed throughout, while a workspace with a desk and chair is neatly arranged nearby.
Flat in Broad Brook
4.88 out of 5 average rating, 110 reviews

Modern Cozy Studio | Walk to Opera House & Eats

Experience the perfect stay in this cozy studio, nestled in the heart of Broad Brook. You'll be conveniently close to local restaurants, the Opera House, and just a short drive from Bradley International Airport, Hartford, CT, and Springfield, MA. Plus, we're pet-friendly! Enjoy direct access to Mill Pond and easy ground-level entry. There are no additional cleaning costs. As an added bonus, a portion of your stay supports St. Jude Children’s Research Hospital!

Top guest favourite
Home in Agawam
4.97 out of 5 average rating, 231 reviews

Sunrise on the Water's Edge - Riverside Bungalow

Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

Top guest favourite
A spacious outdoor area is showcased, featuring a well-maintained lawn and a wooden deck leading to a white, single-story house. Surrounded by trees, the private yard includes a white picket fence, providing a sense of seclusion.
Guest suite in South Windsor
4.87 out of 5 average rating, 263 reviews

Premium Private Suite • Entry • Wrkspace • Parking

Welcome 🙏 to our premium private guest suite, designed for comfort, privacy, and a seamless stay. Enjoy a spacious, hotel-style retreat with a separate private entrance, easy self check-in, fast Wi-Fi, dedicated workspace, and free parking—ideal for couples, business travelers, and extended stays. Quiet, beautifully maintained, and thoughtfully designed for a stress-free experience 😊.

Top guest favourite
Home in West Suffield
4.97 out of 5 average rating, 123 reviews

Linny’s Lake House - with dock

Linny’s Lake House & Dock Access 🌲🌳 Charming Lakeside Home on South Pond Welcome to our newly renovated lake house tucked into a peaceful 3/4-acre wooded lot, naturally treated to keep mosquitoes and ticks to a minimum. The setting feels calm and restorative, with gentle breezes, shaded trees, and the charm of nearby tobacco fields adding to the sense of being away without being remote.

Top guest favourite
The charming stone cottage features a vibrant blue door and flower boxes filled with colorful plants. Lush greenery surrounds the entrance, and original brick walkways lead to the home. Sunlight filters through the trees, creating a welcoming atmosphere outside.
Guest house in Granby
4.98 out of 5 average rating, 899 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Top guest favourite
Flat in Tolland
4.96 out of 5 average rating, 335 reviews

Cozy studio loft

Cozy studio apartment in a quiet, wooded setting in Tolland, CT—just minutes from I-84 and 15 minutes to UConn. Sleeps 2–4 with a queen bed and optional mattress. Includes full kitchen, bathroom, fast Wi-Fi, private entrance, and easy self check-in. Free Level 2 EV charging and plenty of parking. Ideal for short or extended stays. No pets, no smoking, no parties.

Guest favourite
A bright living area features a dark sofa with multiple cushions, flanked by two patterned chairs. A wooden coffee table is positioned in the center, and a laptop is placed on it. Natural light enters through the two windows, adorned with dark curtains.
Flat in Enfield
4.99 out of 5 average rating, 310 reviews

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.

Popular amenities for East Windsor holiday rentals