Photo by Richard Miska

Search Sheffield Island Cottages

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Cottages in Sheffield Island

Our top choices for Sheffield Island cottages

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (92)
"Jeff was easy to work with and we had a wonderful stay. Perfect location for Graduation weekend. Very good location and quiet. Would recommend. "
Westport "Gold Coast" across from Southport beach

South Salem Vacation Rental w/ Furnished Deck!

10.0 out of 10, Exceptional, (2)
"This was the second time I stayed at this property and really do love it. It is close enough to my family in Ridgefield for me to fee like I am just around the corner, while being in a quiet, peaceful private property. The setup was perfect for myself and my mom, but could also accommodate a larger group. It isn’t a big space, but had everything that we needed. I would highly recommend this property and will definitely be looking to stay here again on another visit. Thank you!"
South Salem Vacation Rental w/ Furnished Deck!

Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
$442 nightly
The price is $505
Aug 25 - Aug 26
Total with taxes and fees
Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

Charming 1 bedroom Stony Brook cottage -walking distance to village & university

10.0 out of 10, Exceptional, (3)
"Loved the property. Clean small space. Perfect for a couple! "
Charming 1 bedroom Stony Brook cottage -walking distance to village & university

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (16)
"Great time, nice little private neighborhood! Pretty views if you go for nice walks. 2 great parks near by. Lovely stay. Had everything we needed "
Second floor cottage apartment located in a private community.

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

10.0 out of 10, Exceptional, (9)
"Wonderful stay!"
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

Charming Fairfield Beach 3BR 2BA Cottage By The Sea

10.0 out of 10, Exceptional, (32)
"Gerard was very responsive and helpful and the rental was lovely and in a great location. The beach access was great as were the beach accessories we could borrow! The house stayed nice and cool in during the hot days! Would stay again."
Charming Fairfield Beach 3BR 2BA Cottage By The Sea

Beach cottage on private beach!

10.0 out of 10, Exceptional, (4)
"It was a very nice cottage. Great price for staying right on the beach"
Beach cottage on private beach!

Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington

9.4 out of 10, Exceptional, (6)
"Beautiful quiet neighborhood. Extremely clean apartment. Nice yard. Air conditioning was great. Missing some supplies like silverware etc. "
Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

2.0 star property
10.0 out of 10, Exceptional, (3)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (12)
"Perfect for my needs. Would stay again for sure"
Trendy 1 bedroom +loft apartment w/ parking

Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!

3.0 star property
Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!

Beach house cottage steps to private beach in the heart of Bayville

10.0 out of 10, Exceptional, (10)
"Great location. Very clean modern cottage by the sea. Would love to stay again. "
Beach house cottage steps to private beach in the heart of Bayville

Beachfront cottage located in the heart of Fairfield Beach!!

9.6 out of 10, Exceptional, (17)
"I grew up here! Always fun"
Beachfront cottage located in the heart of Fairfield Beach!!

Cozy Riverside Cottage

10.0 out of 10, Exceptional, (3)
"Check-in was very simple. The neighborhood very quiet and walkable along the bay. All the amenities were available plus extras. The host was super and always reachable, much appreciated. We plan on staying again soon!!"
Cozy Riverside Cottage

Sun and Fun on the beach!!

9.6 out of 10, Exceptional, (17)
"Perfect beach and outdoor life for young kids! Such a great relaxing long weekend - the house had everything we needed. Hoping for another stay soon!"
Sun and Fun on the beach!!

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

9.4 out of 10, Exceptional, (3)
"A cozy, well-maintained cottage, conveniently located near our son and his family who we were visiting. Modern appliances in the kitchen. Exterior and interior were as shown on VRBO. The property manager and owner were very helpful whenever we needed anything. Highly recommended. We would definitely like to stay here again whenever we visit our son."
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

Cozy cottage in charming Pound Ridge with WiFi, AC

Cozy cottage in charming Pound Ridge with WiFi, AC

Quiet Commack Cottage w/ Pool, 8 Mi to Beach!

3.0 star property
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!

Glen Cove Home: Walk to Boardwalk + Dining!

3.0 star property
Glen Cove Home: Walk to Boardwalk + Dining!
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

Top Sheffield Island Hotel Reviews