
Holiday rentals with outdoor seating in Windsor
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Windsor
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

HideAway UConn Coventry RockFarm BnB Breakfast A+
Welcome to “The Hide Away” on Rock Farm with Superhosts Jon & Jeri. A private, family-friendly 1000+ sq ft wooded retreat featuring two bedrooms, 500 Mbps WiFi, Roku TV, private deck, full kitchen, laundry, and DIY breakfast. Just 15 minutes to UConn and 2 minutes to Bolton Lakes for fishing and hiking. See our VIP Guest Book for local favorites. Clean, cozy, no-shoe secluded BnB — 5⭐️ guest favorite. Ask about “The GetAway” too! It’s our King Studio Suite, a private space, perfect for couples.

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.

Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Hidden Cozy Waterfront Eco Cabin Nature Sanctuary
Welcome to Otter Falls Inn! Nestled in the trees directly above the brook and hidden off the main road sits our cozy, vintage eco cottage. Just 8 minutes from all major conveniences, our property is a hidden oasis- an urban nature sanctuary where we are restoring native habitat and the waterway. We lovingly restored and updated the cottage to offer a unique, relaxing, romantic getaway where guests can slow down and enjoy connecting to each other and nature in this stylish, eco conscious home.

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,

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.

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.

Premium Private Suite • Entry • Wrkspace • Parking
Welcome 🙏 to our premium private guest suite, designed for comfort, privacy, and a seamless stay. Enjoy a spacious, hotel-style retreat with a separate private entrance, easy self check-in, fast Wi-Fi, dedicated workspace, and free parking—ideal for couples, business travelers, and extended stays. Quiet, beautifully maintained, and thoughtfully designed for a stress-free experience 😊.

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

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!

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.

Treehouse - Countryside - Farm Animals - Fire Pit
Escape to the stars in the Private Treehouse nestled among the trees at Bluebird Farm Connecticut. Amenities: ● 100+ Mbps Wi-Fi | Outdoor Fire Pit | Indoor Fireplace ● Interaction w/ Farm Animals | Year-Long Running Water (Sink/Shower) ● Kitchenette | AC in Unit | Free Coffee | Board Games | Books Drive To UCONN (10 Mins) | Hartford (30 Mins) | Boston (1 Hour) | NYC (2.5 Hours)
Popular amenities for outdoor seating rentals in Windsor
House rentals with outdoor seating

Farm Fresh Feeding Hills

Classic Lakehouse~Fire Pit_Canoes_Kayaks & Sunsets

Luxe Bolton Lake

Best River View, on Rail Trail in Collinsville!

Prime West Hartford Center Location: Historic Gem

Litchfield County Farmhouse with a Modern Twist

Nature Lovers Retreat-Wine Vineyards Skiing nearby

Vintage 3BR Farmhouse | Near Town + Mount Holyoke
Apartment rentals with outdoor seating

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

West Main

Quiet & Cozy Main Street Retreat

West Hartford Center Apartment 2

Charming apartment with breathtaking view!

Sunny Peaceful Home

2 BR LR 1BA Private In-Law Suite with Home Theater

Western Mass Retreat!
Apartment rentals with outdoor seating

Spa Dreams

Meadow View

Spacious Condo • Quick Drive to Everything

Cozy 3-Bed 2-Bath Condo | Parking and Laundry!

The Vacay Villa

Peaceful Oasis steps from Mohegan Sun

Norwich spa retreat on golf course near casinos

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf
Quick stats about holiday rentals with outdoor seating in Windsor

Total holiday rentals
Explore 10 holiday rentals in Windsor

Nightly prices starting at
Windsor holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 930 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Windsor holiday rentals include wifi access

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

4.9 Average rating
Windsor stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a washing machine and dryer Windsor
- Rentals with a firepit Windsor
- Family-friendly rentals Windsor
- Rentals with a fireplace Windsor
- Rentals with a patio Windsor
- House rentals Windsor
- Pet-friendly rentals Windsor
- Rentals with outdoor seating Connecticut
- Rentals with outdoor seating United States
- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- Ocean Beach Park
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Mohegan Sun
- Bash Bish Falls State Park
- Kent Falls State Park
- Hammonasset Beach State Park
- Mohawk Mountain Ski Area
- Powder Ridge Mountain Park & Resort
- Mystic Seaport Museum
- Mount Southington Ski Area
- Taconic State Park
- Yale University Art Gallery
- Sleeping Giant State Park
- Ski Sundown
- Norman Rockwell Museum
- Naumkeag
- Ocean Beach
- Mystic Aquarium
- Berkshire Botanical Garden
- University of Connecticut




