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.

Simsbury Holiday Rentals

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.
Check In Check Out
    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}
    View Map
    Price
    per night
    £163 Average
    £0£1,000+
    Suitability
    More filters
    All 13 Rentals in Simsbury
    Sort by:
    Default
    Don't let other travellers get your favourite Simsbury area holiday rental. You're so close to securing your perfect getaway. Book today.
    The following rentals are within 40 kilometres of Simsbury.
    East Longmeadow, MA
    1 Review
    1 Bedroom, Sleeps 2Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Torrington
    3 Reviews
    1 Bedroom, Sleeps 2Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Bloomfield
    4 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    West Springfield, MA
    2 Bedrooms, Sleeps 9Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Grill
    • Wi-Fi
    • Satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lily's Lodge is your Home away from Home in Western Massachusetts. We are located directly across the street from the Eastern States Exposition Fairgrounds, minutes from downtown Springfield and within 5-15 minute drive to area colleges, Basketball Hall of Fame, and Six Flags. We provide our...
    View all property information
    Location Information
    West Springfield, Massachusetts 01089
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    Granville, MA
    3 Bedrooms, Sleeps 6Quick View
    other traveller has booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Grill
    • Central Heating
    • Washer
    • Satellite TV
    • DVD Player
    • Housekeeping Included
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 01034
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Cromwell
    1 Review
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Hot Tub
    • Washer
    • Secure Parking
    • Air Conditioning
    • Outdoor Dining Area
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 15 September 2015
    I loved staying at this comfortable home. The area, Middletown CT is centrally located and the home,on Rolling Green is centrally located. It's about 20 minutes from everywhere...
    See all reviews
    About this property
    This house is bright and cheerful even during winter months due to the large paladian windows and cathedral ceilings.<BR>If you find that you are traveling to Connecticut for work assignment or vacation, consider this option to hotel living.<BR>Our home will welcome you from travel or work with...
    View all property information
    Location Information
    Cromwell, Connecticut 06457
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Barkhamsted
    6 Bedrooms, Sleeps 12Quick View
    other traveller has booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Grill
    • Waterfront
    • Patio
    • Porch
    • Satellite TV
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 06063
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
    Make Enquiry
    Agawam, MA
    Studio, Sleeps 5Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Parking
    • DVD Player
    • Air Conditioning
    • Patio
    • Satellite TV
    • Internet Access
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visit Agawam in comfort when you stay at this cozy vacation rental studio that sleeps 5, only a few minutes drive south from Springfield! Complete with a well-equipped kitchen, a plush queen-sized bed and a cozy lounge area with a flat-screen cable TV, this studio is perfect for families and...
    View all property information
    Location Information
    Agawam, Massachusetts 01001
    Condo/Apartment - 1 Bathroom, Sleeps 5
    Make Enquiry
    Litchfield
    3 Bedrooms, Sleeps 7Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Parking
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relish in the luxuries and comforts of this 3-bedroom, 2-bathroom vacation rental house in Litchfield! 'Stone-Peca' is a quintessential New England property that sits on a half acre of land and offers a spacious backyard with a deck and patio. Stylish, high-end decor adorns the interior, making...
    View all property information
    Location Information
    Litchfield, Connecticut 06750
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Winsted
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Satellite TV
    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lake house totally rebuilt in 2016 to high standards. Very warm in cold months, central air in summer. Waterski in Summer, snow ski in winter at nearby local ski mountains (Sundown and Mohawk). Choice location on beautiful lake with full boating. Dockage for your boat directly in front of...
    View all property information
    Location Information
    Winsted, Connecticut 06098
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Portland
    1 Bedroom, Sleeps 2Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Washer
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 97201 2249
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Litchfield
    3 Bedrooms, Sleeps 5Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set on the edge of a valley with westerly views on a beautiful street in Litchfield this vintage home has all modern amenities and style. Has a well in the mudroom and the steep staircase to give you a really authentic 1820's retreat. A large park-like yard with old granite barn foundations and...
    View all property information
    Location Information
    Litchfield, Connecticut 06759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Meriden
    Studio, Sleeps 2Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely, Spacious, bright and outward room studio with fireplace for a relaxing or romantic getaway. The fireplace area is a favorite spot for people, who enjoy quiet, relaxing and private time. The studio also comes with a modern, fully equipped bathroom, Laundry and plenty of closet space. LBGTQ...
    View all property information
    Location Information
    Meriden, Connecticut 06450
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property
    Owner log in