Holiday Rentals in Windsor

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Holiday Rentals in Windsor

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

9.4 out of 10, Exceptional, (23)
"Right off the highway, very clean and kitchen was very well equipped. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Island Vibes Home

9.4 out of 10, Exceptional, (19)
"Our stay was great! We enjoyed the clean and spacious bedrooms! Super easy and everything was as listed. "
Island Vibes Home

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

2.0 star property
10.0 out of 10, Exceptional, (15)
"Really wonderful stay! The owners were very quick in replaying to any of my questions. The place was very clean and super cute! Would recommend and would stay again! "
The price is €153
includes taxes & fees
17 Aug - 18 Aug
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

Charming Chicopee Getaway

The price is €256
includes taxes & fees
9 Sept - 10 Sept
Charming Chicopee Getaway

Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

10.0 out of 10, Exceptional, (68)
"From booking through check out everything about our experience was amazing! The host was very responsive and helpful with any questions I had. The space was very clean and the host had thought of everything guests could need. We will definitely book again when we travel to the area!"
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.4 out of 10, Exceptional, (8)
"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. "
The price is €144
includes taxes & fees
31 Aug - 1 Sept
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Owner didn’t respond to messages and there was issues with the virtual key QR code However after check in everything was wonderful and I had no issues "
The price is €150
includes taxes & fees
24 Aug - 25 Aug
Cozy apartment in charming Hartford with AC, WiFi

3-bedroom house in perfect Springfield with WiFi, AC

2.0 star property
9.2 out of 10, Wonderful, (5)
3-bedroom house in perfect Springfield with WiFi, AC

PICON COZY

7.4 out of 10, Good, (68)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is €146
includes taxes & fees
22 Aug - 23 Aug
PICON COZY

HOMEY HOMEY

3.4 out of 10, (3)
"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."
The price is €147
includes taxes & fees
16 Aug - 17 Aug
HOMEY HOMEY

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (21)
"very peaceful, amazing view!"
The price is €251
includes taxes & fees
14 Aug - 15 Aug
River Overlook - Check the view from your deck!

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

10.0 out of 10, Exceptional, (58)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is €431
includes taxes & fees
18 Aug - 19 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

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

10.0 out of 10, Exceptional, (1)
"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."
The price is €369
includes taxes & fees
7 Sept - 8 Sept
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (31)
"This a the most unique place! A very clean and comfortable apartment above a barn with beautiful horses and more. Wonderful hosts too. We hope to be back! "
Mountaintop Horse Farm with Heated Pool

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

2.0 star property
6.6 out of 10, (4)
"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!"
Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa

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

9.6 out of 10, Exceptional, (32)
"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. "
The price is €276
includes taxes & fees
18 Aug - 19 Aug
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

10.0 out of 10, Exceptional, (1)
"Smooth and straightforward check-in process. They were accommodating to our schedule and communicated everything in a timely manner. House was clean and everything looked as listed. Kitchen was well stocked with up to date appliances and plenty of utensils which was a nice surprise. Plenty of space for 7 of us, would suggest bringing an air mattress though if with a larger party. Overwhelming positive experience overall. "
The price is €440
includes taxes & fees
15 Aug - 16 Aug
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Modern Condo|DWNTN Hartord| XL Center| GYM

4.0 out of 10, (2)
"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."
The price is €181
includes taxes & fees
13 Aug - 14 Aug
Modern Condo|DWNTN Hartord| XL Center| GYM

Modern Luxury, The Perfect Getaway Awaits

10.0 out of 10, Exceptional, (2)
"Super clear, spacious, house looks just like the photos. Very easy communication with the host. Thank you!"
The price is €495
includes taxes & fees
19 Aug - 20 Aug
Modern Luxury, The Perfect Getaway Awaits

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

9.0 out of 10, Wonderful, (42)
"It was a very cozy stay"
The price is €318
includes taxes & fees
2 Sept - 3 Sept
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Windsor?

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

What are some of the best holiday rentals that Windsor has to offer?

3-bedroom house in perfect Springfield with WiFi, AC: This holiday home rental outside of Windsor has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Windsor?

Expedia has 6 holiday rentals for your stay in Windsor.

What can I see and do in Windsor?

Cultural attractions include Windsor Arts Center and Windsor Historical Society, 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 holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.