Windsor Vacation Rentals from ￥9,530: Search Short-Term Rentals

Q: What's the top vacation rental that Windsor has to offer?

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs : This vacation home rental outside of Windsor is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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Vacation Rentals in Windsor

Cozy living room with a comfortable sofa, coffee table, and fireplace.

"Right off the highway, very clean and kitchen was very well equipped. "

Enjoy meals in the kitchen with a central island and dining area, perfect for casual gatherings.

"Our stay was great! We enjoyed the clean and spacious bedrooms! Super easy and everything was as listed. "

Relax in this spacious room with a high ceiling and comfortable seating area.

"This property had easy access to the lake and had nice character. it was a quick overnight and wished we had more time to enjoy it. Kitchen pots and pans and bath towels could be updated. Bathroom door needs attention as its hard to close."

￥63,152 total

includes taxes & fees

Aug 6 - Aug 7

Kitchen features a white stove, cabinetry, and a coffee maker.

￥49,917 total

includes taxes & fees

Aug 2 - Aug 3

Relax in style with a comfortable sofa, tufted armchair, and sleek coffee table.

"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "

￥48,388 total

includes taxes & fees

Jul 31 - Aug 1

Relax on the covered porch with a comfortable seating area and beautiful views.

"The house and location were perfect. Comfortable beds! Would definitely stay again"

Cozy apartment with a kitchenette, featuring a stove, sink, and cabinets. The room includes a bed with a wooden frame, two windows, and a small table with a chair.

￥24,928 total

includes taxes & fees

Jul 27 - Jul 28

Enjoy a compact yet functional space with a kitchenette, dining area, and cozy living space featuring a sofa and flat-screen TV.

"I am impressed with the Lux Private Loft. Absolutely Gorgeous!!. I hope to return. The kitchen area, enormous shower, large screen t.v. I will book again as soon as possible."

￥28,988 total

includes taxes & fees

Aug 1 - Aug 2

Enjoy cooking in this fully equipped kitchen with a microwave, coffee maker, and refrigerator.

"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "

￥23,325 total

includes taxes & fees

Jul 28 - Jul 29

Enjoy cooking in this well-equipped kitchen with a microwave, coffee maker, and coffee machine.

"The location was fantastic.Check-In, Parking and Check-Out easy.The images of the condo were misleading.- cockroaches were present- Floors were not swept- sofa bed sheets were still on bed and unwashed- makeup on the pillow cases from the pullout couch and the hair dryer bag- bedside furniture had broken drawers- one kitchen chair was extremely wobbly- kitchen table light did not workWe will not staying here again."

￥31,473 total

includes taxes & fees

Jul 27 - Jul 28

Surrounded by lush greenery, this serene property features a beautifully maintained front yard with flowering shrubs and a neatly trimmed lawn.

"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."

￥53,476 total

includes taxes & fees

Jul 27 - Jul 28

Relax on the deck with a cozy seating arrangement, featuring a gazebo and comfortable furniture.

"Beautiful lake, traditional charming cottage- great get-away"

Enjoy cooking in this well-equipped kitchen with a stainless steel range hood, black oven, and white refrigerator.

"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."

￥78,021 total

includes taxes & fees

Jul 28 - Jul 29

"I'd like to say that upon arriving the house was beautiful. There's a gorgeous backyard pond with a water spout in the middle. A nice accessible driveway and a cute little cobblestone walkway leading up to the entrance of the guest house. It was beautiful when we arrived inside. House was clean and inviting and there was also cold water and refreshments. Will 100% be booking again... I would give it a hundred stars if I could. Best experience ever."

Enjoy a compact yet functional space with a kitchenette, dining area, and living space.

"I was a little worried to be right in downtown with just me and my daughter. But this location was very safe and cute shopping area around the apartment. "

￥23,914 total

includes taxes & fees

Aug 3 - Aug 4

Relax in a cozy seating area with a sofa and table, overlooking a scenic view.

"As advertised, great communication, would stay there again!"

Relax by the pool surrounded by lush greenery and a traditional house in the background.

"We had the best time with the farm animals, great pool and unbelievable views"

Stairs lead to an upper floor with a neutral-toned wall and a metal railing.

"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."

￥24,527 total

includes taxes & fees

Jul 26 - Jul 27

Enjoy meals in this kitchen with a microwave, stainless steel range hood, and dining area with a table and chairs.

"Communication with the host was excellent. His place was clean, bright, and very well equipped! The location makes it easy to get around the greater Hartford area. Our stay was very good!"

Enjoy cooking in this well-equipped kitchen with a stove, sink, and dishwasher.

"Everything about the house and property was exactly as described. We had the best time there with plenty of space to spread out. It was very clean and comfortable. The kids had so much fun exploring and they visited the ice cream shop everyday that it was open.We will definitely stay here again."

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Top Windsor Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent

"It was quiet and I loved the pool. Good service "

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, there are vacation rentals where you'll be just 13 mi (21 km) from Six Flags New England, providing a more remote option if you want peace and quiet. Visitors like the top-notch restaurants and shops in Windsor. Allow some time to check out the theme park during your trip.

What's the top vacation rental that Windsor has to offer?

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs: This vacation home rental outside of Windsor is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Windsor?

Expedia has 6 vacation rentals for your stay in Windsor.

What can I see and do in Windsor?

Cultural attractions include Windsor Arts Center and Oliver Ellsworth Homestead, whereas Keney Park and Northwest Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Loomis Chaffee School and Farmington River.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can stay in for a short or long stay in Windsor. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.

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Windsor Vacation Rentals

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Vacation Rentals in Windsor

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Island Vibes Home

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Charming Chicopee Getaway

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Bring Your Pet & Visit Springfield: Westfield Home

Cozy apartment in charming Hartford with AC, WiFi

Lux Boutique Large Private LOFT Pratt St Hartford

PICON COZY

Modern Condo|DWNTN Hartord| XL Center| GYM

Big farmhouse in the foothills of the Berkshires

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Charming, Large Cozy 1-bedroom house in fabulous Berlin with WiFi, near Hartford

Totally Private Cozy studio in awesome Hartford with WiFi, AC

5 bedroom in the center of Springfield .

Mountaintop Horse Farm with Heated Pool

HOMEY HOMEY

Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa

Charming Farmhouse w/ Pool & Fishing Pond!

Top Windsor Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

Marriott Hartford/Windsor Airport

Hampton Inn & Suites Hartford/East Hartford

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Best Western Manchester

MGM Springfield

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

The Capitol Hotel

Holiday Inn Express & Suites Bradley Airport by IHG

Find out more about Windsor

Frequently asked questions