Skip to content
Sign up
Log in
Vacation rentals in Cheshire

Vacation rentals in Cheshire

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Cheshire

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Wintergreen Gardens, at the William Becroft House
    SUPERHOSTEntire guest suite · 2 guests · 1 bed · 1 bathroom
    Wintergreen Gardens, at the William Becroft House

    My 2-night minimum does not apply to previous guests (message me). Our 1915, LGBTQ friendly, Arts & Crafts bungalow's private spacious in-law suite offers driveway parking, private entrance, king bedroom, en-suite bath, kitchenette w/refrige, micro, coffee maker and TV. Sunroom opens onto private patios for sunning, morning coffee or a nook to read a book. Walk downtown for outdoor dining or a drink. 5 min. drive to two vineyards. Check out my guidebook for food/entertainment recommendations.

    What guests are saying:

    “This Airbnb is the antithesis to standard vernaculars and sets itself apart as a quintessential accommodation. Various textures and materials are elegantly and thoughtfully joined together in an atmosphere of conviviality. Depth of details throughout are provocatively distinct, nuanced, and charmingly shaped offering an exceptional user experience. A home in total harmony.”

  • Private Room in Upscale Modern Home
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bathroom
    Private Room in Upscale Modern Home

    Perfect room for Choate, Yale, and Quinnipiac visitor. Close to I-91 and the center of Wallingford. Minutes from two beautiful vineyards and local parks. Private room with bathroom. We have a black labrador retriever that lives in the house. (Dog allergies beware) Keypad home entry. Television and WiFi available. We live in the home so we will most likely meet&greet you when you arrive! I always check in with you upon arrival on your scheduled day. I require contact before arrival.

    What guests are saying:

    “Great stay and wonderful hostess! I frequently book at Amy's when I am in the Wallingford area. The room is spacious and welcoming. Love having my own bathroom and refrigerator. Highly recommend!”

  • Guest room in suburban circle near Wesleyan Univ.
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1.5 shared bathrooms
    Guest room in suburban circle near Wesleyan Univ.

    Welcome to my home located in a suburban residential neighborhood only 1.5 miles from Wesleyan University. Guest room with queen bed is ideal for one or two guests. Parking for one car available in my driveway. I am self-employed and work at home, so I will be nearby if you need anything.

    What guests are saying:

    “Very comfortable home in quiet neighborhood in Middletown. Quite convenient for those needing to be at Wesleyan, Middlesex Hospital, or anything else in town.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Cheshire holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Cheshire

Luxurious Lake Home
SUPERHOSTEntire house
Luxurious Lake Home
Price:€244 / night
Pops of Color Retreat in large Tudor home
SUPERHOSTPrivate room
Pops of Color Retreat in large Tudor home
Price:€34 / night
Fair Haven Heights Entire 1 Bedroom Apartment
Entire flat
Fair Haven Heights Entire 1 Bedroom Apartment
Price:€53 / night
Quiet 1 bedroom on Wesleyan campus walk to freeman
SUPERHOSTEntire flat
Quiet 1 bedroom on Wesleyan campus walk to freeman
Price:€66 / night
FREE AMENITIES/AWESOME SPACE/NEAR DOWNTOWN
SUPERHOSTPrivate room
FREE AMENITIES/AWESOME SPACE/NEAR DOWNTOWN
Price:€28 / night
Barry's Horse Getway
SUPERHOSTPrivate room
Barry's Horse Getway
Price:€160 / night
Spacious, comfortable, convenient to QU and Yale
SUPERHOSTPrivate room
Spacious, comfortable, convenient to QU and Yale
Price:€44 / night
Furnished farmhouse 2nd floor private apartment
SUPERHOSTEntire flat
Furnished farmhouse 2nd floor private apartment
Price:€52 / night
Quaint 2br apt- walk to Wesleyan and Main Street
SUPERHOSTEntire house
Quaint 2br apt- walk to Wesleyan and Main Street
Price:€90 / night
Spacious downstairs apartment
SUPERHOSTEntire guest suite
Spacious downstairs apartment
Price:€59 / night
Studio
SUPERHOSTPrivate room
Studio
Price:€40 / night
Private Apartment Near Wesleyan University
Entire flat
Private Apartment Near Wesleyan University
Price:€40 / night
Show all