Short-Term Rentals in Windsor, CT: Compare 10+ Sites & Save

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45 Best Short-Term Rentals in Windsor (Starting from $115)

Lovely Ranch House in Windsor, 10 mins to Hartford Connecticut
Lovely Ranch House in Windsor, 10 mins to Hartford Connecticut
House
Windsor, CT, USA
2.1k from Windsor center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

2 Bedrooms5 Guests
7.7

Good

20 reviews

$167
Average price / night
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Beautiful Spacious Loft Style Townhome, 10 mins from train station and airport!\n
Beautiful Spacious Loft Style Townhome, 10 mins from train station and airport!\n
House
Windsor, CT, 06095, United States
3.0k from Windsor center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

New to Booking
$176
Average price / night
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Vintage Windsor Home Private Yard and Covered Deck
Vintage Windsor Home Private Yard and Covered Deck
House
Windsor, CT, USA
6.0k from Windsor center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
9.0

Fabulous

1 reviews

$172
Average price / night
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Island Vibes Home
Island Vibes Home
House
Windsor, CT, 06095, United States
3.4k from Windsor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
9.6

Exceptional

21 reviews

$253
Average price / night
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East Granby with AC and WiFi 3 minute to Bradley
East Granby with AC and WiFi 3 minute to Bradley
House
CT, USA
6.8k from Windsor center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms8 Guests
New to Booking
$351
Average price / night
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Fully Furnished 4BR Executive Home / Corporate, Insurance & Travel Professionals
Fully Furnished 4BR Executive Home / Corporate, Insurance & Travel Professionals
House
Windsor, CT, 06095, United States
3.8k from Windsor center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Living Area, Microwave, No Smoking

4 Bedrooms6 Guests
New to Booking
$247
Average price / night
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Spacious home away from home
Spacious home away from home
House
Bloomfield, CT, USA
7.5k from Windsor center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Jacuzzis, Places to stay

5 Bedrooms8 Guests
New to Booking
$381
Average price / night
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Landing | Beautiful 2BD, Clubhouse, Gym
Landing | Beautiful 2BD, Clubhouse, Gym
Apartment
Windsor, CT, 06095, United States
4.1k from Windsor center

AC, Balcony, Heater, Internet, Kitchen, No Smoking, TV, Washer

2 Bedrooms4 Guests
New to Booking
$152
Average price / night
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Charming 3 bedroom 2 bath home in Bloomfield with wishing well
Charming 3 bedroom 2 bath home in Bloomfield with wishing well
House
Bloomfield, CT, USA
7.5k from Windsor center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$259
Average price / night
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Landing | Stylish 2BD, Pool, Courtyard
Landing | Stylish 2BD, Pool, Courtyard
Apartment
Bloomfield, CT, 06095, United States
4.1k from Windsor center

AC, Balcony, Heater, Internet, Kitchen, No Smoking, TV, Washer

2 Bedrooms4 Guests
New to Booking
$138
Average price / night
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Convenient Hartford Condo Less Than 2 Mi to Dtwn!
Convenient Hartford Condo Less Than 2 Mi to Dtwn!
Apartment
Stowe Village Housing Project, CT, USA
9.7k from Windsor center

Fireplace/Heating, Accessibility, Security/Safety, Internet, Guest Services, Parking, Child Friendly

1 Bedroom4 Guests
New to Booking
$176
Average price / night
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Beautiful 2-bedroom apartment with AC in cool Windsor
Beautiful 2-bedroom apartment with AC in cool Windsor
Apartment
Windsor, CT, 06095, United States
4.9k from Windsor center

AC, Heater, Living Area, No Smoking

2 Bedrooms5 Guests
New to Booking
$278
Average price / night
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Fall in Love with New England Charm this Fall!!!
Fall in Love with New England Charm this Fall!!!
Apartment
Windsor, CT, 06095, United States
5.1k from Windsor center

AC, Barbecue, Fitness Equipment, Free Parking, Heater, Microwave, No Smoking, TV

1 Bedroom6 Guests
New to Booking
$196
Average price / night
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NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
House
Windsor, CT, 06095, United States
5.1k from Windsor center

AC, Free Parking, Heater, Internet, Kitchen, Living Area, No Smoking, TV

2 Bedrooms4 Guests
9.4

Superb

33 reviews

$175
Average price / night
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2-bedroom apartment in welcoming Windsor with AC and comfort.
2-bedroom apartment in welcoming Windsor with AC and comfort.
Apartment
Windsor, CT, 06095, United States
5.3k from Windsor center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms5 Guests
New to Booking
$221
Average price / night
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1BR/1.5BA Entire Loft Condo near Bradley Airport 30+ days
1BR/1.5BA Entire Loft Condo near Bradley Airport 30+ days
Condo
Windsor Locks, CT, 06096, United States
5.4k from Windsor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$115
Average price / night
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Spacious Guest Apartment in the quiet suburbs of Hartford
Spacious Guest Apartment in the quiet suburbs of Hartford
Apartment
Bloomfield, CT, 06002, United States
5.6k from Windsor center

AC, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
10.0

Exceptional

81 reviews

$131
Average price / night
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Spacious Yard w/ Gazebo: Charming Windsor Retreat
Spacious Yard w/ Gazebo: Charming Windsor Retreat
House
Windsor, CT, 06095, United States
5.8k from Windsor center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Kitchen, Microwave

4 Bedrooms9 Guests
9.4

Superb

11 reviews

$436
Average price / night
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A “Wow” Experience everywhere there is something to stimulate your mind Interest
A “Wow” Experience everywhere there is something to stimulate your mind Interest
House
Windsor, CT, 06095, United States
5.8k from Windsor center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$382
Average price / night
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Vintage Windsor Home: Private Yard & Covered Deck
Vintage Windsor Home: Private Yard & Covered Deck
House
Windsor, CT, 06095-4224, United States
6.0k from Windsor center

AC, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
8.4

Very Good

12 reviews

$212
Average price / night
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Quiet Comfy Getaway 3 BDR home. Close to Bradley Airport.
Quiet Comfy Getaway 3 BDR home. Close to Bradley Airport.
House
Windsor, CT, 06095, United States
6.0k from Windsor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
9.4

Superb

3 reviews

$247
Average price / night
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Charming 1-bedroom apartment with WiFi, AC in brilliant East Windsor
Charming 1-bedroom apartment with WiFi, AC in brilliant East Windsor
Apartment
East Windsor, CT, 06088, United States
6.7k from Windsor center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, Pool

1 Bedroom3 Guests
New to Booking
$209
Average price / night
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Relaxing Retreat w/Sweet Yard!
Relaxing Retreat w/Sweet Yard!
Apartment
Bloomfield, CT, 06002, United States
6.8k from Windsor center

AC, Dryer, Free Parking, Heater, Internet, Microwave, No Smoking, Washer

1 Bedroom6 Guests
New to Booking
$675
Average price / night
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Charming East Granby house with AC and WiFi 3 minutes to Bradley Airport
Charming East Granby house with AC and WiFi 3 minutes to Bradley Airport
House
East Granby, CT, 06026, United States
7.0k from Windsor center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$425
Average price / night
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Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.
House
Windsor Locks, CT, 06096, United States
7.3k from Windsor center

AC, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$448
Average price / night
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Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
House
Bloomfield, CT, 06002, United States
7.5k from Windsor center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

5 Bedrooms10 Guests
9.0

Fabulous

6 reviews

$607
Average price / night
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Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
House
Bloomfield, CT, 06002, United States
7.6k from Windsor center

AC, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking

10 Bedrooms16 Guests
New to Booking
$1299
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Windsor.

Windsor Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 45 verified short-term rentals in Windsor, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Windsor vary depending on location, property size, and travel dates. Rates typically start from around $115 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Windsor include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Windsor, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Windsor often include amenities such as Fireplace/Heating, Wellness Facilities, and Bedding/Linens, providing a comfortable and convenient stay.

Short-term rentals in Windsor are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.