
Vacation rentals in Windsor
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness, and more.

Designer's Den in the Business District
The Quintessential Hartford Experience!! Historic building in the heart of Hartford's Business District makes the "Designer's Den" a truly unique city-living experience. Big city vibes in a stylish corner unit with views of the Capital building & Bushnell Park. The unit is very nicely appointed with all the creature comforts you can imagine (+blackout curtains) . The Elevator makes grocery-hauling in the city easy. Located within walking distance of the very best downtown Hartford has to offer!

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

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

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.

Private Cozy Suite, 0 Fees, Pets Allowed, EV Plug
A private cozy suite for you! Better than a hotel or private room & less than an entire house. Pets welcome with no fees :) Generous discounts for medium- to long-term stays. Your guest suite includes newly furnished living room, apartment kitchenette, large bedroom with full bathroom. Despite many renovations, we kept the vintage & cozy charm. Separate Wifi for remote work. Less than 20 minutes to the airport and Hartford metro. No cost EV charger on site. No cleaning fees!

Modern Cozy Studio
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!

Relax By The Water
Take it easy at this unique and tranquil getaway. Just 20 minutes from downtown Hartford, 5 minutes from Bradley airport, and conveniently close to the Loomis Chaffee school, you’ll have our entire two bedroom, two bath riverfront home to enjoy. Take in the views from the expansive balcony, enjoy a meal in the waterside dining room, or work from home in the dedicated office space. Two queen beds and a sleeper sofa sleep six comfortably. Don’t miss it!

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.

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.

Private 1 BR Suite in West Hartford CT Home
Private 1 BR Queen Suite with large living room, full kitchen, 1.5 Baths and separate entrance. Ideal for long-term stays. Quiet residential neighborhood close to West Hartford Center and Elizabeth Park. Quick drive to U of Hartford, Trinity College, UConn Law/Medical, St. Francis and Hartford Hospitals. Two blocks to pizza, bakery, market & liquor store.

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.

Pet Friendly Cozy Home for Work/Leisure
Great for work travellers or vacationers!Enjoy a stylish experience at this centrally-located place. Welcome to a safe and pretty neighborhood with parks, restaurants, and stores nearby, we have tried our best to incorporate technology with warmth and creativity for your comfort. Forget your worries in this spacious and serene pet friendly space!
Popular amenities for Windsor vacation rentals
Stay near Windsor's top sights
Other great vacation rentals in Windsor

Room for rent in multi family (Rm 1B)

Cozy private room .

Exquisite Bedroom near I-91 with high speed Wi-Fi

Private suite in James Colt townhouse

PVT. ROOM in Charming Home outside Dtwn Hartford.

Simple living in Suffield

Charming & Cozy

Quiet, clean home, private room and bath
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ426 | ﺩ.ﺇ452 | ﺩ.ﺇ441 | ﺩ.ﺇ496 | ﺩ.ﺇ415 | ﺩ.ﺇ386 | ﺩ.ﺇ400 | ﺩ.ﺇ441 | ﺩ.ﺇ466 | ﺩ.ﺇ444 | ﺩ.ﺇ459 | ﺩ.ﺇ485 |
| Avg. temp | -3°C | -1°C | 3°C | 10°C | 16°C | 20°C | 24°C | 23°C | 18°C | 12°C | 6°C | 0°C |
Frequently Asked Questions
Where should I stay in Windsor?
Make yourself at home in Windsor by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in Hayden, and over 70 vacation rentals in Windsor Locks.
Do house rentals in Windsor have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Windsor. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Windsor?
Experience the best of Windsor with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Windsor?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with free parking, over 30 homes with a kitchen, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Windsor have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Windsor?
Windsor has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Windsor have wifi?
Absolutely! We offer over 30 house rentals with wifi in Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Windsor?
Yes! Work meets play with ease at over 40 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Windsor?
Four-legged friends are welcome in Windsor. Choose from more than 20 vacation rentals for guests traveling with pets.
Do house rentals in Windsor have free parking?
Absolutely! We offer over 30 house rentals with free parking in Windsor. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Windsor

Total vacation rentals
Explore 70 vacation rentals in Windsor

Nightly prices starting at
Windsor vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 1,850 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
70 of Windsor vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Windsor rentals

4.7 Average rating
Windsor stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- The Hamptons Vacation rentals
- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- Ocean Beach Park
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Kent Falls State Park
- Butternut Ski Area and Tubing Center
- Mohawk Mountain Ski Area
- Mohegan Sun
- Taconic State Park
- Mount Southington Ski Area
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Mystic Seaport Museum
- Sleeping Giant State Park
- Norman Rockwell Museum
- Yale University Art Gallery
- Berkshire Botanical Garden
- Ski Sundown
- Naumkeag
- University of Massachusetts Amherst
- Bluff Point State Park
- Wesleyan University




