
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.

Norbrook Farm ~ Rustic farmhouse w/ pond & trails
Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

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.

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.

Hot Tub & Cloud Ceiling House 5 min to Mohegan Sun
Stay at a one-of-a-kind house located 5 minutes from Mohegan Sun and several other attractions close by. Our house is conveniently located close to Foxwoods, Mystic, vineyards, Navel Submarine Base, Ct College, USCG Academy and several beaches. Enjoy our game room where you can play arcade games, pool, foosball, giant connect 4, hooky, board games and sing karaoke all under a light up cloud ceiling. Relax in the hot tub or by the gas fire pit in our private backyard.

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!

Litchfield County Farmhouse with a Modern Twist
Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.

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 Getaway-HOST & Co.

Cedar Ridge: House

Hilltop House - HOST & Co.

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

Grand 9 BR Near Casinos
Weekly house rentals

Charming Cape Home, Close to All

By The River

The Majestic View | Luxury Stay Golf Views

Relax By The Water

Best River View, on Rail Trail in Collinsville!

A Beauty by the Park| 3 beds 1 Ba

South Quarter House

Home near Six Flags/ hot tub
Private house rentals

Pet Friendly Cozy Home for Work/Leisure

Nest&Rest Escape

The Hangar

Lake House Retreat Granby CT

5 Bd 2.5 Bth Home Away From Home

Hillside Haven

Charming Cottage next to Flamig Farm

Perfectly located cozy 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 | €112 | €121 | €121 | €126 |
| 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





