A rocky shoreline with calm water and a clear sky.

Sherwood Island State Park Holiday Rentals

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Our top choices for Sherwood Island State Park holiday 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 NZ$463
includes taxes & fees
28 Sept - 29 Sept
DUNE Fairfield Beach

2. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (181 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is NZ$339
includes taxes & fees
27 Sept - 28 Sept
Stamford Suites

3. 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 NZ$671
includes taxes & fees
22 Oct - 23 Oct
Guesthouse at Norwalk Inn

4. 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 NZ$1,265
includes taxes & fees
21 Oct - 22 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

5. 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 NZ$1,012
includes taxes & fees
21 Oct - 22 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

6. 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 NZ$1,120
includes taxes & fees
24 Sept - 25 Sept
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

7. 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.
The price is NZ$1,153
includes taxes & fees
23 Sept - 24 Sept
Nama-stay, sweet pink Saugatuck Shores beach cottage

8. 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 NZ$1,310
includes taxes & fees
22 Sept - 23 Sept
4 Mi to Beach & Dtwn! Charming Fairfield Home

9. 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 NZ$404
includes taxes & fees
24 Sept - 25 Sept
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

10. 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 NZ$442
includes taxes & fees
22 Sept - 23 Sept
Spacious Studio with Pool Table

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 NZ$758
includes taxes & fees
4 Oct - 5 Oct
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

12. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.4 out of 10, Exceptional, (20 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
The price is NZ$1,649
includes taxes & fees
20 Oct - 21 Oct
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

13. 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 NZ$1,273
includes taxes & fees
22 Sept - 23 Sept
4 Mi to Beach & Dtwn! Charming Fairfield Home

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 NZ$454
includes taxes & fees
22 Sept - 23 Sept
Centric property close to all the great things in the city

15. 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
9.8 out of 10, Exceptional, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is NZ$576
includes taxes & fees
30 Sept - 1 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

16. Elite room stay

Elite room stay
Bridgeport
The price is NZ$582
includes taxes & fees
22 Sept - 23 Sept
Elite room stay

17. Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
8.8 out of 10, Excellent, (10 reviews)
"Plenty of bedrooms and space for the family. Very prompt communication with host."
United States
David K.
The price is NZ$2,203
includes taxes & fees
20 Oct - 21 Oct
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

18. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NZ$2,618
includes taxes & fees
23 Sept - 24 Sept
Beechmont - Perfect for Family Retreat!

19. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is NZ$748
includes taxes & fees
28 Sept - 29 Sept
Gilded Age Luxury Surrounded by Nature

20. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, Exceptional, (2 reviews)
"A great location. We were less than 15 minutes from everything we did. House was a super layout for our large group."
United States
Mark F.
The price is NZ$1,480
includes taxes & fees
14 Oct - 15 Oct
Spacious Retreat with Game Room and Fire Pit
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sherwood Island State Park holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sherwood Island State Park. 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 Sherwood Island State Park. 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 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 holiday 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 Sherwood Island State Park short-term rentals, that won’t be hard to do.

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