Hot Windsor Cottage Rates

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Featured Cottages in Windsor

Charming Cottage by the Lake❤️

Charming Cottage by the Lake❤️

Coventry CT
Stay at this cottage in Coventry. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Nathan Hale Homestead and J. M. ...
Opens in a new windowCharming Cottage by the Lake❤️
Step back in time with our 2-bedroom cottage in charming New Hartford!

Step back in time with our 2-bedroom cottage in charming New Hartford!

New Hartford CT
Stay at this cottage in New Hartford. Enjoy laundry facilities, patios and air conditioning. Popular attractions Brodie Park and Ledgebrook Plaza are located ...
Opens in a new windowStep back in time with our 2-bedroom cottage in charming New Hartford!
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

East Hampton CT
Stay at this cottage in East Hampton. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Day Pond State Park and Comstock Bridge are located ...
Opens in a new windowFamily-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
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Waterfront Cottage at Highland Lake w/dock

Waterfront Cottage at Highland Lake w/dock

Winsted CT
Stay at this cottage in Winsted. Enjoy free Wi-Fi, a garden and patios. Popular attractions The Marina at Highland Lake and Winchester Historical Society are ...
Opens in a new windowWaterfront Cottage at Highland Lake w/dock
Lake Getaway at Coventry Lake! close to Uconn

Lake Getaway at Coventry Lake! close to Uconn

Coventry CT
Stay at this cottage in Coventry. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions J. M. Sarnik & Sons' The Old General Store and Nathan ...
Opens in a new windowLake Getaway at Coventry Lake! close to Uconn
Westfield Vacation Rental w/ Porch, Pets Welcome!

Westfield Vacation Rental w/ Porch, Pets Welcome!

3 out of 5
Westfield MA
Stay at this cottage in Westfield. Enjoy free parking and air conditioning. Popular attractions Stanley Park and Woodward Center are located nearby.
Opens in a new windowWestfield Vacation Rental w/ Porch, Pets Welcome!
Backyard Tiny House in the Woods

Backyard Tiny House in the Woods

Tolland CT
Stay at this cottage in Tolland. Enjoy laundry facilities, in-room fireplaces and air conditioning. Popular attractions Crystal Peat Conservation Area and Charter ...
Opens in a new windowBackyard Tiny House in the Woods
Lakefront Tranquility/Fishermans Delight

Lakefront Tranquility/Fishermans Delight

New Hartford CT
Stay at this cottage in New Hartford. Enjoy free Wi-Fi, a garden and patios. Popular attractions Brodie Park and Jerram Winery are located nearby.
Opens in a new windowLakefront Tranquility/Fishermans Delight
Vintage Windsor Home: Private Yard & Covered Deck

Vintage Windsor Home: Private Yard & Covered Deck

3 out of 5
Windsor CT
Stay at this business-friendly cottage in Windsor. Enjoy free parking and air conditioning. Popular attractions Loomis Chaffee School and Windsor Arts Center ...
Opens in a new windowVintage Windsor Home: Private Yard & Covered Deck
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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.

Windsor Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Windsor will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Windsor definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Windsor, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Windsor Cottages essential information

Accommodation
36 Cottages
Lowest Price
NZ$219
Highest Price
NZ$386
Popular accommodation
Charming Cottage by the Lake❤️, Step back in time with our 2-bedroom cottage in charming New Hartford!, Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!, Waterfront Cottage at Highland Lake w/dock, Lake Getaway at Coventry Lake! close to Uconn, Westfield Vacation Rental w/ Porch, Pets Welcome!, Backyard Tiny House in the Woods, Lakefront Tranquility/Fishermans Delight, Vintage Windsor Home: Private Yard & Covered Deck

Top trending hotels in Windsor

Marriott Hartford/Windsor Airport

Marriott Hartford/Windsor Airport

3.5 out of 5
28 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
The price is NZ$386 per night from 10 May to 11 May
NZ$386
10 May - 11 May
includes taxes & fees
Stay at this business-friendly hotel in Windsor. Enjoy free parking, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
Opens in a new windowMarriott Hartford/Windsor Airport
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
100 Dunfey Ln Windsor CT
Fully refundableReserve now, pay when you stay
The price is NZ$219 per night from 25 May to 26 May
NZ$219
25 May - 26 May
includes taxes & fees
Stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowResidence Inn by Marriott Hartford/Windsor
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
200 Corporate Dr Windsor CT
Fully refundableReserve now, pay when you stay
The price is NZ$291 per night from 25 May to 26 May
NZ$291
25 May - 26 May
includes taxes & fees
Stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowHYATT house Hartford North/Windsor
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Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
555 Corporate Dr Windsor CT
Fully refundableReserve now, pay when you stay
The price is NZ$246 per night from 25 May to 26 May
NZ$246
25 May - 26 May
includes taxes & fees
Stay at this business-friendly hotel in Windsor. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowHilton Garden Inn Hartford North/Bradley Int'l Airport
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.