Pet-friendly vacation rentals in Windsor

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Top-rated pet-friendly home rentals in Windsor

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
A spacious living area is presented, featuring a comfortable gray sectional sofa, a wooden coffee table, and a decorative rug. Two green bar stools are positioned at a small counter, and a ceiling fan is mounted above, enhancing the cozy atmosphere of the penthouse apartment.
Home in West Hartford
4.9 out of 5 average rating, 108 reviews

WeHa Penthouse w/ Private Deck

Welcome to our cozy penthouse-style apartment, where comfort meets tranquility. Enjoy a private deck with exceptional views of West Hartford. Treat yourself with our minibar and indulge without leaving your unit. Centrally located, our apartment provides easy access to the best of West Hartford. Explore Blue Back Square, a vibrant dining hub just 5 minutes away. For a leisurely experience, walk 2 minutes to Park Rd and discover culinary delights like Plan B, Americano Bar, and Zaytoon’s Bistro.

Top guest favorite
A charming cottage features wood shingle siding and a neatly arranged entrance. The front yard showcases a manicured area with green grass, accompanied by a duck and a chicken. Nearby, expansive fields and a rustic barn complete the serene rural landscape.
Guesthouse in Portland
4.98 out of 5 average rating, 253 reviews

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Guest favorite
Cabin in Bloomfield
4.97 out of 5 average rating, 133 reviews

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.

Top guest favorite
A contemporary lakefront home is surrounded by tall trees, with a spacious deck offering views of Middle Bolton Lake. A fire pit is situated on a stone patio, surrounded by Adirondack chairs. The lush green yard leads to the water's edge, enhancing the natural ambiance.
Home in Vernon
4.99 out of 5 average rating, 164 reviews

Luxe Bolton Lake

Lakefront jacuzzi for fall! Relax and enjoy the stylish comfort of our 3 bedroom/3 bathroom architecturally-designed lake home. The Luxe lake house features an expansive waterfront, outdoor jacuzzi, gorgeous primary bedroom suite w/ private shower and tub, artistic furniture, cozy fireplace, coffee bar, complimentary snacks, fast WiFi, large deck, fire pit, kayaks, vintage aluminum canoe, board games, and much more. Come stay at the Luxe lake house and make memories that will last a lifetime!

Guest favorite
The bedroom features a spacious bed with white bedding, complemented by a wooden desk and chair. Two windows with light-filtering shades allow natural light to enter, while a world map adorns the walls. Built-in storage and warm hardwood flooring add to the room's charm.
Guest suite in Bloomfield
4.92 out of 5 average rating, 113 reviews

Private Cozy Suite, 0 Fees, Easy CheckIn, EV Plug

A private cozy suite for you! Better than a hotel or private room & less than an entire house. We do not charge extra fees! Sizable discounts for medium- to long-term stays. Your guest suite includes newly furnished living room, apartment kitchenette, large bedroom with full bathroom. Heating, cooling and hot water are all-electric. Despite many renovations, we kept the vintage & cozy charm. Separate Wifi for remote work. Less than 20 minutes to the airport and Hartford metro. EV charger!

Guest favorite
A cozy living room features a stone fireplace surrounded by purple walls. A wooden table sits at the center, adorned with a decorative bowl. A comfortable sofa and a wooden chair are positioned near the fireplace, complementing the warm ambiance.
Cottage in Windsor
4.9 out of 5 average rating, 196 reviews

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.

Top guest favorite
Two sheep sit comfortably on a bed of soft wood shavings. Their woolly coats provide contrast, with one sheep displaying a predominantly white fleece and the other featuring a patch of black on its face. The interior of a vehicle is visible in the background.
Guest suite in Granby
4.95 out of 5 average rating, 108 reviews

Onomea Farm

Relax and watch the sheep graze in the pasture. Enjoy the amazing night sky. Fabulous modern two bedroom handicapped accessible in law suite with separate entrance. Fireplace, washer/dryer, heat, central A/C. Queen bed on main level, King and pull out sofa on 2nd floor. Both bedrooms have 50” TV’s. Full kitchen. Located in North Granby, CT. Quiet location yet close to major attractions and Bradley airport. We have 8 resident well behaved dogs THAT RUN FREE on the property -

Guest favorite
A welcoming entrance features a maroon front door with glass panes, flanked by a wooden railing. A slight wooden ramp leads up to the door, surrounded by a manicured area of small plants and gravel, creating an inviting first impression.
Home in Feeding Hills
4.89 out of 5 average rating, 999 reviews

Farm Fresh Feeding Hills

Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, ok for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

Guest favorite
A brick patio area is seen with two rocking chairs positioned beside vibrant orange and yellow flower pots. A welcoming wreath adorns the double doors, and a pumpkin is placed on the ground, enhancing the seasonal decor.
Guest suite in East Granby
4.85 out of 5 average rating, 375 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

Guest favorite
The exterior of a charming red schoolhouse and accessory building is surrounded by vibrant foliage. A white wooden fence outlines the property, leading to a gravel pathway. The buildings feature classic architectural details, with windows framed in white and a backdrop of lush trees.
Cottage in Granby
4.89 out of 5 average rating, 219 reviews

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.

Guest favorite
A globe rests on a polished surface, accompanied by a wooden 'Hello!' sign. Sheer curtains filter soft light, creating a bright and welcoming scene. The composition offers a blend of decorative elements that enhance the living space.
Home in South Windsor
4.9 out of 5 average rating, 165 reviews

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,

Guest favorite
The open living space features a kitchen island with a granite countertop and wooden cabinetry. A dining set with high chairs is positioned nearby. A comfortable blue sofa and a television stand are visible in the living area, complemented by hardwood flooring throughout.
Apartment in Manchester
4.96 out of 5 average rating, 103 reviews

Cozy 1 bedroom clean and quiet

Experience the charm of Manchester CT in this fully furnished 1 bedroom apartment! Available now. Pet-friendly, with laundry facilities conveniently located within the unit. Enjoy easy access to highways from this centrally located apartment while being just minutes away from quaint downtown area amenities.

Popular amenities for Windsor pet-friendly home rentals

Quick stats about vacation rentals that are pet-friendly in Windsor

  • Total vacation rentals

    Explore 20 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at $50 per night before taxes and fees

  • Verified guest reviews

    Over 700 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Windsor vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor rentals

  • 4.6 Average rating

    Windsor stays receive an average rating of 4.6 out of 5 from guests

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