We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals, Apartments and Homes in Windsor, CT

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    €0
    €202 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Windsor area holiday rental. You're so close to securing your perfect getaway. Book today.

    The following rentals are within 40 kilometers of Windsor, Connecticut.

    1 / 9
    4.5 of 5 stars (3) Very good
    Coventry
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 21
    5 of 5 stars (1) Excellent
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 20
    5 of 5 stars (1) Excellent
    Middletown
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    1 / 15
    Barkhamsted
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Grill
    • Waterfront
    • Patio
    • Porch
    • Satellite TV
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Nestled on the banks of the Farmington River, Legends offers comfortable rooms in a lodge setting with river views, breakfast Thursday -Sunday, healthy afternoon snacks and a special homemade juice of the day. All rooms offer AC, private bath, TV and internet. Fly-fishing,hunting kayaking, hiking,... View all property information
    Location Information
    Barkhamsted, Connecticut
    1 / 9
    Stafford Springs
    1 Bedroom, 4 Bathrooms, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    This is the Green Room with private bath and queen bed, perfect for the couple who wants to Practice a screenplay and maybe even experience some paranormal activity. not for the faint of heart! Shooting balls of light, orbs, apparitions and whistlers may be experienced. Practice your dance routine,... View all property information
    Location Information
    Stafford Springs, Connecticut
    1 / 17
    Middlefield
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Parking
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Private Garden
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautiful newly remodeled cottage is located on Lake Beseck in picturesque Middlefield, Ct. The views of the lake are serene and produce an immediate feeling of tranquility. This is a family home and has all the amenities that you need to feel at home including a complete kitchen. Betty's Boat... View all property information
    Location Information
    Middlefield, Connecticut
    1 / 20
    Farmington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 370383 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Compass Furnished Apartments at this property is located in Farmington, CT, just... View all property information
    Location Information
    Farmington, Connecticut
    1 / 4
    Bloomfield
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Central Heating
    • Washer
    • Porch
    • Parking
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Nice get away. Come see our hard wood floors in the living rm, bedrooms (2), with bath & Eat- in kitchen and enjoy your own washer & dryer Hook-Up and storage areas in your own basement. These units are equipped with OIL Heat, Electric hot water and stove. A must see with All Utilities are... View all property information
    Location Information
    Bloomfield, Connecticut
    1 / 32
    Middlefield
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Grill
    • Waterfront
    • Private Garden
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Clarke's Landing is newly built 2 story lakefront house with heat and air conditioning! It is a family home and has all the amenities that you would have at home.Everything is NEW! It includes cable and WiFi internet, new quality linens, paper goods, shampoo,spices, beach towels, chairs , floats... View all property information
    Location Information
    Middlefield, Connecticut
    1 / 13
    Granville, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Grill
    • Central Heating
    • Washer
    • Satellite TV
    • DVD Player
    • Housekeeping...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Would you like to spend some time in our cozy retreat in the Berkshires? Our three-bedrooms, two bathrooms house is located in a private community, in the middle of the Tolland state forest , surrounded by the woods and lakes, but at the same time close to major attractions. Fully renovated, the... View all property information
    Location Information
    Granville, Berkshires
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 11
    Portland
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Washer
    • Sauna
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    One bedroom, furnished, deluxe condo in the core of Portland, Oregon…with fantastic views of the West Hills, PSU, and Downtown Portland. The condo is just East of the Portland State University Campus. Rented on a month by month basis. Convenient to all aspects. Attributes: √ Near the top of the... View all property information
    Location Information
    Portland, Connecticut
    1 / 20
    Farmington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 370406 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Compass Furnished Apartments at this property is located in Farmington, CT, just... View all property information
    Location Information
    Farmington, Connecticut
    1 / 3
    Farmington
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Terrace
    • Patio
    • Air Conditioning
    • Balcony
    • Private Outdoor...
    • Porch
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    magnificant French Normandy hillside all brick 6 bedroom 7.5 bath custom Mansion with 3.5 acres beautiful, lush, private, exclusive ESTATE, in prestigious FARMINGTON, CT. Just at I-84, Exit 39. May be leased for long weekends, weekly or long term stay. . 6 bedrooms, 7.5 baths, swimming pool,... View all property information
    Location Information
    Farmington, Connecticut
    1 / 39
    Middle Haddam
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Waterfront
    • Patio
    • Internet Access
    • DVD Player
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The Captain's House, a 3,400 SF 3-level renovated waterfront Victorian, features 5 bedrooms, 3-1/2 baths, gourmet kitchen,wraparound deck, tennis court and 40' dock. A magical place to relax & recharge... Knowles Landing is one of the most beautiful waterfront estates on the Connecticut River.... View all property information
    Location Information
    Middle Haddam, Connecticut