Sherwood Island State Park Vacation Rentals

    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 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Sherwood Island State Park Vacation Homes

Captain's Cottage - Cold Spring Harbor Water Views
Smart TV, fireplace, table tennis, computer monitors

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (65)
"Great home to stay. Beautiful area to explore!"
The price is CA $530
CA $972 total
includes taxes & fees
Sep 8 - Sep 9
Captain's Cottage - Cold Spring Harbor Water Views
Stareway to Heaven Su
Terrace/patio

Stareway to Heaven Su

10.0 out of 10, Exceptional, (6)
"We stayed with family at this lovely home for my son’s graduation and Mother’s Day. The home is even nicer than the pictures- everything is top notch. It’s one block from a nice beach with lovely views from many of the rooms. We would love to come back and stay! "
Stareway to Heaven Su
Beautiful historic home in Stony Brook!
Interior

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (12)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.6 out of 10, Exceptional, (4)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield
Business or Weekend escape
Pool

Business or Weekend escape

9.2 out of 10, Wonderful, (44)
"Very nice owner with great communication. "
The price is CA $117
CA $202 total
includes taxes & fees
Aug 18 - Aug 19
Business or Weekend escape
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Marina

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (63)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Minutes to Walnut Beach, newly renovated 3 bedroom home
Sun loungers, beach towels

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (6)
"Very nice place."
Minutes to Walnut Beach, newly renovated 3 bedroom home
Stay at Black Rock Harbor
Exterior

Stay at Black Rock Harbor

10.0 out of 10, Exceptional, (21)
"Lovely home, responsive host & convenient location with water views. Cute & comfy decor with well appointed kitchen and off street parking. "
Stay at Black Rock Harbor
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Exterior

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
The price is CA $419
CA $879 total
includes taxes & fees
Aug 14 - Aug 15
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Beach

Quaint duplex with private yard. Walk to beach, dining, & shopping!

10.0 out of 10, Exceptional, (44)
"Needed a place to stay with our dog while visiting our granddaughters in a nearby town."
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Soothing Carriage House with Hot Tub in charming Stratford
Interior

Soothing Carriage House with Hot Tub in charming Stratford

10.0 out of 10, Exceptional, (2)
"John was a wonderful Host.We had a very relaxing time in the Hot Tub and the carriage house had everything we needed for our stay.We will definitely book again,Lisa and Holly"
Soothing Carriage House with Hot Tub in charming Stratford
Cheerful 4 bedrooms residential house.
Exterior

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (32)
"House was perfect for what we needed. Great proximity to the Amphitheater and Seaside Park. "
Cheerful 4 bedrooms residential house.
Lakeside luxury: beautiful, relaxing 4 bedroom home
Property grounds

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (28)
"This property was perfect for our needs! Checking in and out was simple and easy. The house is spacious and backyard is gorgeous! "
Lakeside luxury: beautiful, relaxing 4 bedroom home
Charming 2-bedroom house with WiFi, AC in Fairfield
Interior

Charming 2-bedroom house with WiFi, AC in Fairfield

8.0 out of 10, Very good, (3)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is CA $204
CA $473 total
includes taxes & fees
Aug 26 - Aug 27
Charming 2-bedroom house with WiFi, AC in Fairfield
Blue Cottage East Setauket
Fridge, microwave, oven, stovetop

Blue Cottage East Setauket

Blue Cottage East Setauket
Charming 3 Bedroom Beach Front Cottage with Fireplace
Fridge, microwave, oven, stovetop

Charming 3 Bedroom Beach Front Cottage with Fireplace

9.4 out of 10, Exceptional, (29)
"Beautiful view / location"
Charming 3 Bedroom Beach Front Cottage with Fireplace
Dulce La Donna by the beach
Beach

Dulce La Donna by the beach

10.0 out of 10, Exceptional, (1)
"The owner is extremely welcoming and communicates very well. "
Dulce La Donna by the beach
Main Street Westport, walk to shops, dining, downtown
Beach

Main Street Westport, walk to shops, dining, downtown

9.0 out of 10, Wonderful, (2)
"Beautiful home, great location, communicative hosts…A"
Main Street Westport, walk to shops, dining, downtown
New Beach Home near Stamford Downtown/Shippan
Terrace/patio

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (21)
"We had a great time and it was a very spacious and clean location "
The price is CA $1,130
CA $1,871 total
includes taxes & fees
Aug 17 - Aug 18
New Beach Home near Stamford Downtown/Shippan
Westport Gem - walk to shops, dining, town center, pet-friendly
Fridge, microwave, oven, dishwasher

Westport Gem - walk to shops, dining, town center, pet-friendly

9.8 out of 10, Exceptional, (8)
"We had a wonderful weekend. Weather was 75-80 and sunny. It is a very clean, beds were very comfortable. Patio was nice with a private back yard. Definitely stay again. "
Westport Gem - walk to shops, dining, town center, pet-friendly
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 Sherwood Island State Park Hotel Reviews

La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

10/10 Excellent
"It was great wonderful staff"
Xiomara 3-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Stamford / New York City