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Search Vacation Homes in Sheffield Island

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Our top choices for Sheffield Island vacation homes

Newly renovated Private bedroom near Stony Brook University

Newly renovated Private bedroom near Stony Brook University
2.0 star property
Stony Brook
8.0 out of 10, Very Good, (2)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
Newly renovated Private bedroom near Stony Brook University

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AED 312
AED 538 total
includes taxes & fees
6 Jan - 7 January 2026
Business or Weekend escape

Marine Theme - 4 BR - Backyard - Fire pit

Marine Theme - 4 BR - Backyard - Fire pit
North End
9.8 out of 10, Exceptional, (8)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is AED 588
AED 1,527 total
includes taxes & fees
16 Dec - 17 Dec
Marine Theme - 4 BR - Backyard - Fire pit

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Greenwich
9.6 out of 10, Exceptional, (23)
"The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. "
United States
Victoria R.
The price is AED 471
AED 979 total
includes taxes & fees
11 Dec - 12 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

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
7.2 out of 10, Good, (13)
"This rental was great accommodation"
United States
Alma B.
The price is AED 578
AED 1,092 total
includes taxes & fees
11 Dec - 12 Dec
Centric property close to all the great things in the city

Bright Escape, Top-Rated Design, Fire pit, Near Beach

Bright Escape, Top-Rated Design, Fire pit, Near Beach
Fairfield
10.0 out of 10, Exceptional, (11)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is AED 713
AED 1,841 total
includes taxes & fees
18 Dec - 19 Dec
Bright Escape, Top-Rated Design, Fire pit, Near Beach

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, (9)
"Lovely little home in Stamford."
United States
Pat A.
The price is AED 578
AED 1,209 total
includes taxes & fees
11 Dec - 12 Dec
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Fairfield
10.0 out of 10, Exceptional, (22)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is AED 749
AED 1,838 total
includes taxes & fees
7 Jan - 8 January 2026
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

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

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
9.4 out of 10, Exceptional, (6)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
United States
April R.
The price is AED 3,223
AED 5,827 total
includes taxes & fees
11 Dec - 12 Dec
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

The B&W Haven 5BR Home with yard theater + Office

The B&W Haven 5BR Home with yard theater + Office
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (8)
"Host was very polite and communicated well throughout the stay. The property appears well maintained. There are window units but everyone was comfortable for the duration of our stay."
United States
George M.
The price is AED 1,051
AED 2,469 total
includes taxes & fees
11 Dec - 12 Dec
The B&W Haven 5BR Home with yard theater + Office

Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Stylish 2BR House Near Stony Brook University and shopping, fully renovated
2.0 star property
Stony Brook
10.0 out of 10, Exceptional, (1)
"perfect place"
New Zealand
Akaki G.
The price is AED 843
AED 1,953 total
includes taxes & fees
11 Dec - 12 Dec
Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is AED 3,108
AED 4,860 total
includes taxes & fees
12 Dec - 13 Dec
Beechmont - Perfect for Family Retreat!

Modern + Spacious 5BR/2BA Home, Renovated Backyard

Modern + Spacious 5BR/2BA Home, Renovated Backyard
West End - West Side
9.6 out of 10, Exceptional, (4)
"Used for family weekend at SHU. Convenient location and plenty of space for the whole family! "
United States
Laurene S.
The price is AED 1,305
AED 2,839 total
includes taxes & fees
11 Dec - 12 Dec
Modern + Spacious 5BR/2BA Home, Renovated Backyard

🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna

🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna
Fairfield
10.0 out of 10, Exceptional, (1)
"The Host was welcoming and responsive to our inquiries!Our stay was wonderful! The property was spectacular and offered all the amenities we needed for a comfortable and enjoyable visit. "
United States
Patricia B.
The price is AED 3,298
AED 7,883 total
includes taxes & fees
17 Dec - 18 Dec
🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna

The Bella Vista St James! Waterfront house with a beach dock and so much more!

The Bella Vista St James! Waterfront house with a beach dock and so much more!
Saint James
10.0 out of 10, Exceptional, (1)
"This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to chase my little around to ensure they weren't touching or playing with any of the decorations. Plenty of bathrooms and counter space. No cell reception but the Wi-Fi worked throughout the whole home....
United States
Devin k.
The price is AED 4,905
AED 7,526 total
includes taxes & fees
11 Dec - 12 Dec
The Bella Vista St James! Waterfront house with a beach dock and so much more!

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, (73)
"Location was perfect!"
United States
Linda J P.
The price is AED 1,139
AED 2,232 total
includes taxes & fees
5 Jan - 6 January 2026
Captain's Cottage - Cold Spring Harbor Water Views

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
2.0 star property
Norwalk
10.0 out of 10, Exceptional, (8)
"We were so pleased with the accommodations. The location is so quiet in a charming neighborhood. The home is well equipped with kitchen supplied and entertainment options. We were delighted to be able to barbecue. Claudia is very responsive and helpful."
Canada
nawab k.
The price is AED 1,017
AED 2,203 total
includes taxes & fees
6 Jan - 7 January 2026
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Bright Stylish Chic 4BR 4BA Home Pet Friendly!
North Stamford
10.0 out of 10, Exceptional, (105)
"Wonderful family home!Everything you need!Beautiful location!Great host!"
United States
Linda T.
The price is AED 1,603
AED 3,456 total
includes taxes & fees
14 Dec - 15 Dec
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

45 Minutes from NYC, Entire House near Stamford Downtown,

45 Minutes from NYC, Entire House near Stamford Downtown,
Downtown Stamford
10.0 out of 10, Exceptional, (21)
"Our hosts were very attentive and responsive with communications. The house is lovely, clean, well stocked and in a great location. We thoroughly enjoyed our stay!"
United States
Megan P.
The price is AED 628
AED 1,415 total
includes taxes & fees
11 Dec - 12 Dec
45 Minutes from NYC, Entire House near Stamford Downtown,

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (3)
"We chose to stay here for a family event nearby. We found the property very clean and comfortable throughout our stay and would not hesitate to book it again. Although this trip wasn’t about adventuring elsewhere, we know it is convenient to many great places in Fairfield County, Connecticut, as well as New York."
United States
Ellen L.
The price is AED 823
AED 1,794 total
includes taxes & fees
14 Dec - 15 Dec
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
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 Sheffield Island Hotel Reviews