Holiday houses in Windsor

Apartment in Downtown Hartford

4.9 out of 5 average rating, 185 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, 133 reviews

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

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

4.9 out of 5 average rating, 191 reviews

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

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.

4.95 out of 5 average rating, 193 reviews

Apartment in New Britain

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

4.99 out of 5 average rating, 684 reviews

Loft in Hartford

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

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

4.89 out of 5 average rating, 199 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.

4.99 out of 5 average rating, 237 reviews

Apartment in Enfield

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.

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

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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Other great holiday rentals in Windsor

Apartment in Downtown Hartford

4.9 out of 5 average rating, 70 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 :))

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.

Apartment in Downtown Hartford

4.92 out of 5 average rating, 52 reviews

Mod-Chic 1 Bedroom with Free Parking & Wifi

ValareeRating, 5 stars2 weeks ago

I really enjoyed my stay. It was easy to access and very clean. I was very comfortable. Had everything I needed.

5 out of 5 average rating, 3 reviews

Home in Enfield

Nest&Rest Escape

DorsenRating, 5 stars3 days 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

4.98 out of 5 average rating, 55 reviews

Relax By The Water

Meera (& Eliot!)Rating, 5 stars3 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!

4.91 out of 5 average rating, 68 reviews

Island Vibes

JodiRating, 5 stars1 week 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!