Vacation rentals in Windsor

4.98 out of 5 average rating, 186 reviews

A private deck area is shown, featuring a sturdy railing and a smooth wooden floor. A comfortable chair is set beside a planter with vibrant flowers. Lush greenery is visible in the background, enhancing the serene atmosphere.

Guest suite in Vernon

Laura's Loft and Gallery, private suite

Unique and roomy space with private entrance, two bedrooms, full bath with tub shower, and plenty of room to relax. Kitchen space has mini fridge, microwave, toaster oven, hot plate, and crock pot. 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 for your breakfast included, and homemade scones in seasonal flavors.

Apartment in Downtown Hartford

A modern elevator door with a red finish is situated against a textured light grey wall. A nearby safety sign indicates emergency procedures, while sleek flooring runs alongside. The surroundings feature minimalistic design elements, contributing to a clean and functional environment.

4.91 out of 5 average rating, 183 reviews

Executive Stay Downtown Hartford

Enjoy a perfect upscale and stylish experience at this centrally located stay in downtown Hartford. With beautiful views of downtown Hartford overlooking our central park known as "The Green", this unit has everything you need (+blackout curtains) . This is Immediately across the street from the XL Center, home of our UCONN HUSKIES, and a short, quick walk from the executive buildings. Come enjoy an amazing stay at one of the premier locations in the city. (Also includes easy parking access.)

5 out of 5 average rating, 132 reviews

The pool area features a clear, inviting swimming pool surrounded by a spacious patio. Lounge chairs are arranged beside the water, and a waterslide is visible at one end. Lush greenery and a fenced yard create a private atmosphere for relaxation and leisure.

Guest suite in Enfield

Luxe 1822 Apt | Rain Shower | Plush beds | Firepit

Oversized 1800sf apartment is a 2-story unit, front half of a 200-year-old former schoolhouse in Enfield's historic district. The antique colonial is set up as a side-by-side duplex with private apartment occupying the front 1/2 of house & the owner's unit in the back with a separate driveway entrance & door. EXTRAS: ❋ PRIVATE USE OF POOL & PATIO ❋ KEYCODE CHECK-IN ANYTIME ❋ COFFEE/TEA BAR WITH EVERYTHING NEEDED ❋ POPCORN MACHINE, SNACKS & DRINKS ❋ 4 TVs: YOUTUBE TV, MAX, NETFLIX, WIFI

Apartment in Windsor Locks

A bedside table positioned beside a wooden bed frame features a small plant in a ceramic pot. A cluster of black notebooks rests on the table, topped by a decorative woven pendant light hanging above, casting gentle shadows on the wall.

4.85 out of 5 average rating, 166 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

4.89 out of 5 average rating, 190 reviews

The bathroom features a modern design with a glass block wall separating the shower area. A sleek sink rests on a dark countertop, complemented by a round mirror above. Soft textiles and a textured rug add comfort to the space.

Cottage in Windsor

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 suite in Bloomfield

A serene outdoor patio is highlighted by two teal chairs positioned around a stone fire pit. A hammock swings gently from a beam, while lush greenery and open sky provide a peaceful backdrop. The textured stone flooring enhances the inviting space.

4.99 out of 5 average rating, 115 reviews

Guest Suite with Private Entrance & View

Relax at our Guest Suite Apartment with a private walk-out entrance on the lower level of our home. Nestled at the end of a quiet neighborhood road our space is just 15 minutes from Bradley Airport & less than an 8-mile drive from Hartford. Have fun with the local bike path, hiking, wineries, and breweries. Afterward, kick up your feet on the queen mattress or unwind on the patio in our peaceful backyard often visited by deer.

4.99 out of 5 average rating, 684 reviews

Loft in Frog Hollow

Loft - Queen Anne Row House in a historic district

Hosted by Judy and Greg, our home is close to art, culture, live theater, and restaurants. Our home is also close to major insurance companies, the state capitol and state of Connecticut offices. You’ll love the cozy 3rd floor loft. We also offer off street parking. Garage space is also available as an option. Our home is a perfect destination for couples, solo adventurers, and business travelers.

Guest suite in East Granby

An iron archway frames a charming garden space filled with various decorative items and plants. A red barn serves as a backdrop, while clouds drift above in a blue sky. Pathways made of stone create a welcoming atmosphere leading into the garden area.

4.85 out of 5 average rating, 357 reviews

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

4.99 out of 5 average rating, 820 reviews

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.

Guesthouse in Granby

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!

4.89 out of 5 average rating, 198 reviews

Cottage in Granby

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.

4.9 out of 5 average rating, 147 reviews

Home in South Windsor

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. Take advantage of 2 full bathrooms. Fully stocked kitchen awaits your inspiration. Many stores are within 10 minutes away from you. BDL is 20 minutes away,

4.85 out of 5 average rating, 145 reviews

A lofted sleeping area is seen above the kitchen, featuring wooden railings and a mattress. The ceiling has a tall, sloped design with green paint, and a ceiling fan is mounted at the peak. Natural light enters through a window adjacent to the kitchen.

Guest suite in Windsor

Rustic Loft Apartment

Cozy studio apartment, minutes from the center of Windsor. Easy access to I-91, grocery stores and Target minutes away. Plenty of off-street parking, private entrance. Laundromat available down the street. The second bedroom is the loft area above the kitchen. The apartment is above a wood working shop.

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Popular amenities for Windsor vacation rentals

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Air conditioning

Other great vacation rentals in Windsor

Apartment in Downtown Hartford

A detailed view of the entrance floor features vintage mosaic tiles in a white hexagonal pattern. The numbers '289' are prominently displayed in a dark green, surrounded by a decorative border of earthy tones.

4.91 out of 5 average rating, 69 reviews

Designer's Den in the Business District

AndreaRating, 5 stars3 weeks ago

Fantastic home! Our host was incredibly friendly and quick to respond. Location is very walkable with lots of things to do and places to eat. Had a few amenity issues but our host was quick to offer alternative options and additional services. Would love to be back :))

A single-story brick house is showcased with a welcoming front yard featuring manicured greenery and blooming flowers. The exterior reflects a blend of stone and brick textures, while a smooth driveway leads to the entrance. Large windows allow natural light to penetrate the living spaces.

4.82 out of 5 average rating, 39 reviews

NEW: Spacious Quaint & Convenient Hideaway!

HeatherRating, 5 stars2 weeks ago

Lynn was great. We had a small issue with the lock on day two but she responded and fixed it in a very timely manner. The house was difficult to see in the dark upon arrival but it was fine once we knew where we were at.

5 out of 5 average rating, 3 reviews

A coffee station is presented with a sleek black coffee maker alongside a selection of tea bags and coffee pods. An array of flavored tea options is visible, providing a choice for guests. A sign humorously states the importance of coffee for enjoyment.

Home in Enfield

Nest&Rest Escape

DorsenRating, 5 stars1 day ago

My girlfriend and I had a truly lovely stay at this B&B. From the moment we arrived, it was clear the space was maintained with great care—the place was absolutely pristine. The amenities were thoughtful and well-appointed, making the entire stay feel effortless and comfortable. We especially appreciated the privacy of the location—it felt like our own peaceful retreat, tucked away just enough to disconnect while still being accessible. The hosts went above and beyond to accommodate us, even setting aside a beautiful arrangement of flowers for my girlfriend’s birthday. It was a thoughtful gesture that did not go unnoticed. Communication was excellent throughout—responsive, clear, and genuinely warm. Every interaction felt intentional, with attention to detail that made us feel welcome and valued. Highly recommended for couples looking for a quiet, intimate escape with top-tier hospitality.

5 out of 5 average rating, 39 reviews

By The River

EhiraRating, 5 stars3 weeks ago

Peaceful place. It looked like the photos. The communication was clear and quick respond. Easy access

A stone exterior corner of the home presents a covered porch with white railings. The adjacent grassy area leads to a serene river view, where trees surround the water's edge, reflecting the soft light of the sky.

4.98 out of 5 average rating, 55 reviews

Relax By The Water

Meera (& Eliot!)Rating, 5 stars2 weeks ago

Bryan and June’s place is peaceful and cozy, and the location by the river is spectacular. The kitchen was really comfortable, clean and usable with lots of cookware and nice quality dishes to eat off of; we easefully made multiple meals together and really enjoyed doing it - which isn’t always the case with Airbnbs. Both bedrooms are lovely, so if you’re in a group that needs both bedrooms, this is a rare find where EVERYONE gets “the nice room.” A rare find!! The beds are comfy and on the softer side, and should work great for 99% of people (they were just fine for my spouse and for our friend who traveled with us). IF you are someone who needs an especially firm and supportive bed due to back issues (my situation, sigh), they may not work for you. I’m only sharing that for anyone else in my very specific position, since I also rely on reviews for info like this!

4.85 out of 5 average rating, 78 reviews

Floating shelves display neatly arranged dishes and glassware, complemented by decorative plants and kitchen essentials. A compact toaster oven rests on the countertop next to a sink, with clean towels folded on the lower shelf, creating a functional and organized kitchenette.

Apartment in Broad Brook

Modern Cozy Studio

KimberlyRating, 5 stars2 weeks ago

Such a perfect place to stay! Looks just like the pictures and is very clean and cozy! Great restaurant and c-store right across the street, dog park in walking distance. Parking is right out front, and there's a perfect lake view in the back. Highly recommend!

Two decorative chairs are positioned in front of a brick fireplace, with a small round table between them. Decorative pillows in shades of turquoise and brown accent the chairs. A coastal scene is depicted in the framed artwork above the fireplace, complementing the natural elements around.

4.91 out of 5 average rating, 68 reviews

Island Vibes

JodiRating, 5 stars5 days ago

This was the perfect home base for our week exploring Connecticut and Massachusetts. It was a quiet location, comfortable and clean space. Close to everything we needed. Would definitely recommend!

A spacious living area features a large sectional sofa adorned with decorative pillows, offering comfortable seating. Large windows allow natural light to fill the room, highlighting the wooden floor and a coffee table at the center. A warm ambiance is complemented by tasteful artwork on the walls.