Sherwood Island State Park Vacation Rentals

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Our top choices for Sherwood Island State Park vacation rentals

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (83 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is CA $235
CA $355 total
includes taxes & fees
Mar 31 - Apr 1
DUNE Fairfield Beach

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (53 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is CA $117
CA $202 total
includes taxes & fees
Mar 28 - Mar 29
Business or Weekend escape

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (18 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is CA $168
CA $247 total
includes taxes & fees
Mar 31 - Apr 1
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.6 out of 10, Exceptional, (8 reviews)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
United States
Caroline
The price is CA $193
CA $319 total
includes taxes & fees
Mar 28 - Mar 29
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (28 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is CA $205
CA $407 total
includes taxes & fees
Mar 31 - Apr 1
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is CA $218
CA $459 total
includes taxes & fees
Mar 30 - Mar 31
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
7.6 out of 10, Good, (4 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is CA $152
CA $213 total
includes taxes & fees
Mar 30 - Mar 31
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford
Milford
8.8 out of 10, Excellent, (3 reviews)
"Had a great stay!"
United States
Garry G.
The price is CA $139
CA $447 total
includes taxes & fees
Mar 30 - Mar 31
Beach Apartment in Woodmont Milford

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
The price is CA $211
CA $447 total
includes taxes & fees
Mar 28 - Mar 29
Zen, Spacious & Comfy 2 bed, Lux beds

Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
7.0 out of 10, Good, (14 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is CA $218
CA $416 total
includes taxes & fees
Apr 1 - Apr 2
Centric property close to all the great things in the city

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is CA $146
CA $400 total
includes taxes & fees
Apr 21 - Apr 22
Renovated 2BR Retreat / Modern Comforts Included

Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22 reviews)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
The price is CA $204
CA $586 total
includes taxes & fees
Apr 1 - Apr 2
Luxury Designer 2 bedroom+office/3bed vacation home.

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very good, (1 review)
"It was clean "
United States
Burton
The price is CA $146
CA $400 total
includes taxes & fees
Mar 28 - Mar 29
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (75 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is CA $300
CA $677 total
includes taxes & fees
Apr 8 - Apr 9
Captain's Cottage - Cold Spring Harbor Water Views

Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102
Milford
The price is CA $87
CA $307 total
includes taxes & fees
Mar 30 - Mar 31
Beach Apartment in Woodmont Milford 102

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"The apartment overall is nice, and located in an area that is close to shops and dining. Listing photos are accurate, but as others have mentioned, this is not a "luxury" apartment. "
United States
Sheree G.
The price is CA $199
CA $435 total
includes taxes & fees
Mar 29 - Mar 30
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (11 reviews)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
The price is CA $290
CA $730 total
includes taxes & fees
Apr 14 - Apr 15
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is CA $196
CA $371 total
includes taxes & fees
Apr 1 - Apr 2
Spacious Studio with Pool Table

Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
6.8 out of 10, (3 reviews)
"Cozy get away"
United States
Anonymous traveller
The price is CA $207
CA $489 total
includes taxes & fees
Mar 29 - Mar 30
Modern 2 Bed in BlackRock

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is CA $269
CA $530 total
includes taxes & fees
Apr 1 - Apr 2
Luxe Provincial Style Studio w/ Patio & Parking
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.
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Top Sherwood Island State Park Hotel Reviews

Find out more about Sherwood Island State Park

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sherwood Island State Park. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.