Sherwood Island State Park Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Sherwood Island State Park vacation rentals

A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (119 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$235 nightly
The price is $270
Nov 22 - Nov 23
Total with taxes and fees
DUNE Fairfield Beach
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

2. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (210 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
$149 nightly
The price is $171
Nov 22 - Nov 23
Total with taxes and fees
Stamford Suites
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

3. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
$298 nightly
The price is $343
Dec 3 - Dec 4
Total with taxes and fees
Guesthouse at Norwalk Inn
A swimming pool at night with blue lighting.

4. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (60 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
$127 nightly
The price is $144
Nov 15 - Nov 16
Total with taxes and fees
Business or Weekend escape
A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

5. 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
9.4 out of 10, Exceptional, (19 reviews)
"A hidden gem! We have stayed here twice now when attending concerts at Hartford Healthcare Amphitheater. A beautifully appointed room within walking distance to the shows!"
United States
Kim F.
$195 nightly
The price is $222
Nov 16 - Nov 17
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A modern kitchen with a white refrigerator, a stove, and a sink. There are four wicker chairs around a white table.

6. Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveler
$264 nightly
The price is $300
Nov 30 - Dec 1
Total with taxes and fees
Renovated 2BR Retreat / Modern Comforts Included
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

7. 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, (29 reviews)
"Great location and clean property. Some items were broken or missing, but overall, a nice stay."
United States
Cherie
$348 nightly
The price is $396
Nov 15 - Nov 16
Total with taxes and fees
Luxury Designer 2 bedroom+office/3bed vacation home.
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

8. Elite room stay

Elite room stay
Bridgeport
$288 nightly
The price is $328
Nov 14 - Nov 15
Total with taxes and fees
Elite room stay
A modern living room with a sofa, a coffee table, and a bar stool.

9. 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)
"loved walking the city. pizza was good."
United States
michelle b.
$263 nightly
The price is $300
Nov 20 - Nov 21
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A neatly arranged bedroom with a bed, bedside table, bench, and wall decor.

10. 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
9.0 out of 10, Wonderful, (2 reviews)
"It was clean "
United States
Burton
$259 nightly
The price is $295
Nov 30 - Dec 1
Total with taxes and fees
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

11. 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
6.8 out of 10, (18 reviews)
"This rental was great accommodation"
United States
Alma B.
$225 nightly
The price is $256
Nov 18 - Nov 19
Total with taxes and fees
Centric property close to all the great things in the city
A covered outdoor seating area with wicker sofas, a fire pit, and string lights.

12. Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (2 reviews)
"Host was attentive and the space was comfortable and exactly what we needed"
United States
Parker M.
$291 nightly
The price is $332
Nov 15 - Nov 16
Total with taxes and fees
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with a kettle, and a painting on the wall.

13. Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay "
United States
Maria Elena G.
$328 nightly
The price is $373
Nov 18 - Nov 19
Total with taxes and fees
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

14. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
8.0 out of 10, Very good, (7 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
$309 nightly
The price is $352
Nov 19 - Nov 20
Total with taxes and fees
Modern 2 Bed in BlackRock
Living area

15. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"Had a lovely stay. Close to the train station and close to things in Stamford. Lovely space and owner was super helpful!"
United States
Marisa C.
$226 nightly
The price is $258
Nov 22 - Nov 23
Total with taxes and fees
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

16. Sunny 1 Full Bed ADA|Free parking

Sunny 1 Full Bed ADA|Free parking
MILFORD
10.0 out of 10, Exceptional, (4 reviews)
"Pool was clean and just right for a quick swim."
United States
Anonymous traveler
$67 nightly
The price is $77
Nov 30 - Dec 1
Total with taxes and fees
Sunny 1 Full Bed ADA|Free parking
A two-story house with a front porch, a chimney, and a well-maintained garden with a stone pathway leading to the entrance.

17. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
$357 nightly
The price is $408
Nov 18 - Nov 19
Total with taxes and fees
Gilded Age Luxury Surrounded by Nature
A two-story house with a front porch, a small garden with various plants, and a tree with red leaves.

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
9.4 out of 10, Exceptional, (35 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
$144 nightly
The price is $165
Nov 15 - Nov 16
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

19. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
$484 nightly
The price is $551
Nov 18 - Nov 19
Total with taxes and fees
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern kitchen with a central island, pendant lights, and built-in shelves.

20. Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
$241 nightly
The price is $274
Dec 1 - Dec 2
Total with taxes and fees
Stylish Home With Free ParkingZA
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

A buffet bar with various food items and a selection of liquor bottles in the background.
Delamar Westport

Delamar Westport

Delamar Westport
Westport

10/10 Excellent

Pool and sauna were an excellent part of the experience. Breakfast buffet was top notch. The moment we arrived, the valet crew and front desk staff made me feel completely relaxed. I knew instantly that I made the right choice booking a stay at Delamar.
United States
James
Reviewed November 9, 2026
Delamar Westport

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