A rocky shoreline with calm water and a clear sky.

Sherwood Island State Park Vacation Rentals

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Our top choices for Sherwood Island State Park vacation rentals

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is CA $250
CA $374 total
includes taxes & fees
Sep 28 - Sep 29
DUNE Fairfield Beach

2. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is CA $401
CA $461 total
includes taxes & fees
Oct 14 - Oct 15
Guesthouse at Norwalk Inn

3. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (182 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is CA $221
CA $255 total
includes taxes & fees
Sep 30 - Oct 1
Stamford Suites

4. 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, (18 reviews)
"The accommodations were incredible. The host provided many helpful materials that made the stay very comfortable. The apartment was very cute and had nice amenities for the guests that go above any beyond what a hotel can provide."
United States
Bailey
The price is CA $197
CA $326 total
includes taxes & fees
Oct 3 - Oct 4
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

5. 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 $202
CA $380 total
includes taxes & fees
Sep 29 - Sep 30
Spacious Studio with Pool Table

6. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.2 out of 10, Wonderful, (17 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
Nama-stay, sweet pink Saugatuck Shores beach cottage

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.6 out of 10, Exceptional, (27 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveller
The price is CA $209
CA $598 total
includes taxes & fees
Oct 6 - Oct 7
Luxury Designer 2 bedroom+office/3bed vacation home.

8. 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.
The price is CA $244
CA $535 total
includes taxes & fees
Sep 28 - Sep 29
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

9. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is CA $643
CA $1,057 total
includes taxes & fees
Oct 6 - Oct 7
4 Mi to Beach & Dtwn! Charming Fairfield Home

10. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (15 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
The price is CA $430
CA $1,011 total
includes taxes & fees
Oct 19 - Oct 20
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

11. King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
The price is CA $423
CA $539 total
includes taxes & fees
Oct 25 - Oct 26
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

12. 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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is CA $316
CA $840 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

13. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (5 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.
The price is CA $190
CA $472 total
includes taxes & fees
Sep 27 - Sep 28
Modern 2 Bed in BlackRock

14. 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
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is CA $222
CA $379 total
includes taxes & fees
Oct 1 - Oct 2
Centric property close to all the great things in the city

15. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
10.0 out of 10, Exceptional, (1 review)
"Beautiful home! Host was super responsive to questions. The entire house was super clean and welcoming. The bed was comfortable and smelled fresh. There was a personalized welcome sign that was a nice touch and some (much needed) snacks after our almost 3 hour drive. Expectations were well within reason and easily manageable. I would 100% rent again."
United States
Raelyn O.
The price is CA $540
CA $1,064 total
includes taxes & fees
Sep 27 - Sep 28
4 Mi to Beach & Dtwn! Charming Fairfield Home

16. 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, (19 reviews)
"Place was very clean . Communication between owner and us was excellent."
United States
gail s.
The price is CA $285
CA $804 total
includes taxes & fees
Sep 28 - Sep 29
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

17. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is CA $434
CA $643 total
includes taxes & fees
Sep 26 - Sep 27
Cozy 1-bedroom house in welcoming Bridgeport

18. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is CA $330
CA $604 total
includes taxes & fees
Oct 6 - Oct 7
Gilded Age Luxury Surrounded by Nature

19. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay."
United States
Linda S.
The price is CA $611
CA $1,178 total
includes taxes & fees
Oct 14 - Oct 15
Spacious Retreat with Game Room and Fire Pit

20. 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, (4 reviews)
"Nice place to stay "
United States
Maria Elena G.
The price is CA $286
CA $622 total
includes taxes & fees
Oct 19 - Oct 20
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
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.

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