
House holiday rentals in Windsor
Find and book unique houses on Airbnb
Quick stats about house rentals in Windsor

Total holiday rentals
Explore 40 holiday rentals in Windsor

Nightly prices starting at
Windsor holiday rentals start at €26 per night before taxes and fees

Verified guest reviews
Over 780 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Windsor holiday rentals include wifi 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
Top-rated house rentals in Windsor
Guests agree: these houses are highly rated for location, cleanliness and more.

Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

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,

Paradise On The Hill Luxury Apartment.
Enjoy your own special and separated section of this beautiful, modern colonial home. This spacious home includes central air, an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large, newly renovated bathroom with spa like jets. His and hers closets. Beautiful fully stocked kitchenette, 2 large screen Smart TVs, 55 inch in living room, 42 inch in bedroom, Free WiFi, dining for 6, all for the comfort and convenience of our guests.

Bright & Private WHOLE HOUSE 4 YOU Near Everything
Welcome to our clean, bright, and private home, just a 15-minute drive from the heart of Hartford! Designed with your comfort and convenience in mind, this cozy retreat is perfect for families, couples, and professionals looking for a peaceful yet central stay! Prime Location, WHOLE HOUSE – Explore New Britain & Beyond! Guest Access: ✔ Private driveway for easy parking ✔ Enclosed garage with keyless entry for secure parking ✔ Keyless pad entry at the front door (host will provide the code)

Island Vibes
Come and enjoy a tranquil stay with an island vibe. This 3 bedroom, 2 bath home will comfortably accommodate up to 8 persons. Large kitchen and living space for everyone. Situated in a quiet suburb on the outskirts of downtown Hartford, it is 12 minutes from Bradley International Airport, 20 minutes from the Basketball Hall of Fame and Springfield Museums Quadrangle. In the region is the Connecticut Science Museum, The Mark Twain House, Wadsworth Atheneum Museum of Art, and much more.

Charming Cape Home, Close to All
Charming Cape Home in the Heart of Connecticut Enjoy comfort and convenience just 20 mins from Bradley Airport, 10 mins from Hartford, 25 mins from UConn, and 40 mins from New Haven. Nestled on a quiet residential street, our cozy home features multiple beds, fast Wi-Fi, Smart TVs, central air, and a fenced backyard with patio and fire pit. Grocery stores, restaurants, and coffee shops are just 5 minutes away. A perfect retreat for families, professionals, or campus visits!

Prime West Hartford Center Location: Historic Gem
Discover the perfect blend of historic charm and modern comfort. Nestled in the heart of West Hartford Center, explore the vibrant Blue Back Square, just a short walk away, offering a variety of shops, restaurants, and entertainment options. The Delamar Hotel is also nearby for added convenience. Step outside onto the expansive deck, complete with a gas fire pit and grill. After each stay, the home undergoes professional cleaning, ensuring a fresh and welcoming experience.

Beautiful Historic Home
The apartment is located in a two-family Historic home situated in Asylum Hills in Hartford. This beautiful historic house was constructed in the year 1880 and used to be uninhabitable until about few years ago when it went through an extensive renovation inside and out. This property is close to many of the top attractions in Hartford such as the Mark Twain House & Museum, Wadsworth Atheneum Museum of Arts, Hartford Stage, Connecticut State Capitol, Dunkin’ Park, and more.

Quiet Comfy Getaway 3 BDR home
Our newly renovated 3-bedroom home offers a comfortable and convenient stay. Perfectly located with easy access to the grocery stores, strip malls, hospitals, and parks, it's an ideal base for your trip. Our home comes with ample parking, pristine kitchen and bathrooms, mini coffee bar, cooking utensils, free WiFi, and a washer/dryer. Stay productive with our dedicated workspace and unwind in our spacious bedrooms. Book now for a home away from home experience!

Best River View, on Rail Trail in Collinsville!
This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

Modern Farmhouse
This is a quaint, sun-filled farmhouse in the Farmington valley of Connecticut. Convenient to great antique shopping, Ski Sundown, farm stands, Farmington river inner-tubing and biking trails, kayak and canoe rentals, the sweet towns of Collinsville and New Hartford, and a 30 minute straight shot to Hartford itself. The house is also convenient to Torrington, Simsbury, Avon, Winsted, and a beautiful drive to Hartford-Bradley International Airport.

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.
Popular amenities for house rentals in Windsor
House rentals with a pool

Breathtaking home with unforgettable views & pool!

The (Quiet Escape) Bradley Airport 6 mins away.

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

Casino Stay & Play House w/Hot Tub, Game Room

mid century ranch style house on farmland

Beauty and the Beach!
Weekly house rentals

Cozy cottage 5 minutes from UConn

By The River

Luxe Bolton Lake

The Majestic View | Luxury Stay Golf Views

Relax By The Water

Private Woodland Sanctuary—3 mins to a lake beach!

Cozy Comforts!

South Quarter House
Private house rentals

Pet Friendly Cozy Home for Work/Leisure

Nest&Rest Escape

The Hangar

A Beauty by the Park| 3 beds 1 Ba

Lake House Retreat Granby CT

Home near Six Flags/ hot tub

Farmhouse Broad Brook: Comfort & Charm.

5 Bd 2.5 Bth Home Away From Home
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €121 | €128 | €121 | €121 | €105 | €105 | €105 | €105 | €111 | €121 | €121 | €125 |
| 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 |
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Baltimore Holiday rentals
- Portland Holiday rentals
- Providence Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Six Flags New England
- Ocean Beach Park
- Mystic Seaport Museum
- Catamount Mountain Ski Resort
- Mystic Aquarium
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Taconic State Park
- Kent Falls State Park
- Hammonasset Beach State Park
- University of Connecticut
- Mohawk Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Yale University Art Gallery
- Ski Sundown
- Ocean Beach
- Soundview Beach
- Wesleyan University
- University of Massachusetts Amherst
- Mount Southington Ski Area





