Windsor Vacation Rentals from CA $92: Short-Term Rentals for 2025

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

"This is such a great property, I spent a whole month with three separate stays adjacent due to travel planning and the host was wonderful. The house is really beautiful and in a great neighborhood and it’s very comfortable and super clean. This will be a regular for me in the Hartford area. I’m looking forward to seeing what the beautiful landscaping is like in the spring and summer too."

"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."

CA $593 total

includes taxes & fees

Jul 21 - Jul 22

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

CA $420 total

includes taxes & fees

Jul 8 - Jul 9

"This was a much needed haven! Frank was very helpful and hospitable. All of the animals were a definite plus! "

CA $231 total

includes taxes & fees

Jul 13 - Jul 14

"Peaceful "

CA $220 total

includes taxes & fees

Jul 8 - Jul 9

"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."

CA $227 total

includes taxes & fees

Jul 8 - Jul 9

"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. "

CA $447 total

includes taxes & fees

Jul 31 - Aug 1

"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."

CA $495 total

includes taxes & fees

Jul 10 - Jul 11

"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."

CA $268 total

includes taxes & fees

Aug 1 - Aug 2

"What a lovely studio!! Checking in and out was so easy. The studio looks just like the pictures. The hosts had everything there that one would need except an iron/board. Quaint little town with limited dining choices but many options near by. We will definitely use this place again."

CA $236 total

includes taxes & fees

Jul 8 - Jul 9

"Had a great time. Ive stayed here multiplt times and keep coming back. Jessica is an amazing host. Very easy to talk to... but they leave you alone. Just an absolutely phenomenal stay"

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

Microwave, electric kettle, cookware/dishes/utensils, paper towels

"Great place in a very nice part of the city. Walkable and lots to do around, and a reasonable parking garage right across the street. Apartment was clean, comfy and easily accessible."

CA $272 total

includes taxes & fees

Jul 13 - Jul 14

"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "

CA $479 total

includes taxes & fees

Jul 22 - Jul 23

"Perfect for everything we needed. Cute and cozy, and 12 miles from our son’s home. Our granddaughter stayed over one of the nights and loved having her own space (she is 4). We Will definitely stay again. "

CA $541 total

includes taxes & fees

Aug 6 - Aug 7

"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."

CA $287 total

includes taxes & fees

Jul 9 - Jul 10

"We had a great time and I would highly recommend for your next stay. Very clean and had everything to make your vacation enjoyable."

CA $618 total

includes taxes & fees

Jul 8 - Jul 9

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

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Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor vacation rentals we have selected for you start as low as CA $92 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Windsor properties

5/5 Excellent

"The staff is so helpful and kind! The hotel was VERY clean. A couple of things to note. There is not breakfast, BUT there is a coffee and tea bar with a different variety of foods such as muffins, yogurts, oatmeal, and fruit! If you are a water drinker, they have free water at reception or they have water for purchase in rooms. Overall, a great stay though! "

A verified traveller stayed at The Goodwin Hotel

Posted 1 day ago

5/5 Excellent

A start of a new family tradition

"Stayed for 2 nights with hubby and daughter for 4th of july weekend to lake compounce only 9 minutes away from this hotel. Service , cleanliness and food was great ,pool was fun. will definitely stay again. Will definitely recommend to friends. They offered free complimentary breakfast buffet from 6am-10am i recomend getting breakfast before 9 as food gets low around that time but there are lots of great choices. Fresh coffee available all day for free. Great time! See you next time"

A verified traveller stayed at Holiday Inn Express Southington by IHG

Posted 1 day ago

5/5 Excellent

Clean Room, great value, and comfortable!

"Recently stayed two nights at the Quality Inn at the end of June. Check in was quick, staff was friendly, and I got my room request, towards the back of the building on a higher floor. I had room 423, it was clean, fairly good condition, everything worked, although fridge took a few hours to cool my drinks, and beds were comfortable. Each queen bed had 3 pillows and I couldn't remember if they used to have 4 each, but I think they did. The room was a great value and there were improvements since my last stay in April. They no longer start clearing breakfast before it ends at 9am, and it was well stocked especially Tuesday morning. Monday morning things were running out and I didn't see staff at all for the last 20 minutes. There was still plenty to eat though. Tuesday, staff kept things full and cleaned the serving area. The AC worked great, decent water pressure, bathroom was clean, and plenty of towels. I overall enjoyed my stay and had no issues. After check out, staff later called as they believed I had left an item behind, and they wanted to figure out how to return it to me, however it wasn't one of my items, but a nice gesture nonetheless! My go to hotel when visiting the area for Six Flags and will continue visiting! Glad to see some improvements! Wish I had more time to take a swim and pool closes at 10pm! Try Tokyo restaurant next door or Wood N Tap down the street for some great dinners! "

A verified traveller stayed at Quality Inn West Springfield

Posted 5 days ago

5/5 Excellent

Absolutely charming

"The Avon Old Farms hotel was an amazing experience. Very welcoming. Places to gather with friends throughout. Friendly staff. Delicious food from Seasons restaurant, which is on site. Eli was my server. He was excellent. Would stay again if I am in that area. Highly recommended. "

A verified traveller stayed at Avon Old Farms Hotel

Posted 6 days ago

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Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, there are vacation rentals close to popular points of interest in Windsor, or you can select a more secluded option if you're looking for relaxation. 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 7 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 Farmington River and Windsor Historical Society.

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

Check prices for these dates

Vacation Rentals in Windsor

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

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

Bring Your Pet & Visit Springfield: Westfield Home

Charming Chicopee Getaway

Mountaintop Horse Farm with Heated Pool

Cozy apartment in charming Hartford with AC, WiFi

PICON COZY

HOMEY HOMEY

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

Big farmhouse in the foothills of the Berkshires

Lux Boutique Large Private LOFT Pratt St Hartford

Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

Charming Boutique Studio suite with everything you need for a getaway

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Blue Back Bungalow

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Modern Condo|DWNTN Hartord| XL Center| GYM

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

5 bedroom in the center of Springfield .

Find out more about Windsor

Recent reviews of Windsor properties

The Goodwin Hotel

Holiday Inn Express Southington by IHG

Hampton Inn & Suites Hartford/East Hartford

The Capitol Hotel

Holiday Inn Express & Suites Bradley Airport by IHG

Quality Inn West Springfield

Best Western Manchester

Avon Old Farms Hotel

MGM Springfield

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Frequently asked questions