Photo by Allison Alano Flores

Search Castles in City Island

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select City Island Castles

Westover Castle -Majestic in The Forest
Outdoor pool, a heated pool

Westover Castle -Majestic in The Forest

10.0 out of 10, Exceptional, (3)
"Awesome stay, property was great and host was very accommodating!"
Westover Castle -Majestic in The Forest
Historic former Speakeasy 4 Bdrm, walk to train and town: Pleasantville
Exterior

Historic former Speakeasy 4 Bdrm, walk to train and town: Pleasantville

Historic former Speakeasy 4 Bdrm, walk to train and town: Pleasantville
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top City Island Hotel Reviews

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

10/10 Excellent
"Great stay. The views are gorgeous "
Danielle 4-night trip
Posted 7 hours ago
PUBLIC, an Ian Schrager hotel