Sheffield Island Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Sheffield Island vacation rentals

Property grounds

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is ￥19,698
￥40,824 total
includes taxes & fees
Mar 8 - Mar 9
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Fridge, microwave, oven, stovetop

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is ￥16,162
￥44,088 total
includes taxes & fees
Feb 17 - Feb 18
Renovated 2BR Retreat / Modern Comforts Included
Exterior

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (18 reviews)
"Perfect spot for a quick trip"
United States
James P.
The price is ￥18,971
￥27,782 total
includes taxes & fees
Feb 17 - Feb 18
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (52 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is ￥12,980
￥22,371 total
includes taxes & fees
Mar 1 - Mar 2
Business or Weekend escape
Smart TV

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
7.0 out of 10, Good, (14 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is ￥24,050
￥45,410 total
includes taxes & fees
Feb 17 - Feb 18
Centric property close to all the great things in the city
Property grounds

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
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥24,050
￥50,258 total
includes taxes & fees
Feb 17 - Feb 18
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Interior

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
10.0 out of 10, Exceptional, (4 reviews)
"Nice little spot with a great host."
United States
J M.
The price is ￥18,629
￥31,654 total
includes taxes & fees
Feb 23 - Feb 24
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Classic Suite | Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (79 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Fridge, microwave, stovetop, cookware/dishes/utensils

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
The price is ￥23,363
￥49,467 total
includes taxes & fees
Feb 18 - Feb 19
Zen, Spacious & Comfy 2 bed, Lux beds
Private kitchen

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is ￥16,797
￥41,963 total
includes taxes & fees
Feb 17 - Feb 18
Elegant Hideaway with Free Parking
Marina

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, (74 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is ￥32,220
￥72,750 total
includes taxes & fees
Feb 23 - Feb 24
Captain's Cottage - Cold Spring Harbor Water Views
Living area

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is ￥18,171
￥43,535 total
includes taxes & fees
Mar 2 - Mar 3
Luxury 3BR Home Game Room Free Parking
2 bedrooms, iron/ironing board, travel crib, WiFi

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
8.0 out of 10, Very Good, (1 review)
"It was clean "
United States
Burton
The price is ￥16,162
￥44,088 total
includes taxes & fees
Feb 17 - Feb 18
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Interior

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, (22 reviews)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
The price is ￥20,676
￥61,036 total
includes taxes & fees
Feb 17 - Feb 18
Luxury Designer 2 bedroom+office/3bed vacation home.
Offices

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)
"The apartment overall is nice, and located in an area that is close to shops and dining. Listing photos are accurate, but as others have mentioned, this is not a "luxury" apartment. "
United States
Sheree G.
The price is ￥21,302
￥40,913 total
includes taxes & fees
Feb 19 - Feb 20
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Property grounds

Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (10 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is ￥23,638
￥59,480 total
includes taxes & fees
Feb 17 - Feb 18
Seabreeze at the beach west beach Stamford ct.
1 bedroom, WiFi

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is ￥29,777
￥58,796 total
includes taxes & fees
Feb 18 - Feb 19
Luxe Provincial Style Studio w/ Patio & Parking
TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (30 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is ￥33,594
￥56,937 total
includes taxes & fees
Feb 17 - Feb 18
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Fridge, microwave, oven, stovetop

Renovated Cape Near beach, with Fire Pit and BBQ

Renovated Cape Near beach, with Fire Pit and BBQ
Fairfield
10.0 out of 10, Exceptional, (11 reviews)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
The price is ￥25,043
￥71,250 total
includes taxes & fees
Feb 23 - Feb 24
Renovated Cape Near beach, with Fire Pit and BBQ
2 bedrooms, WiFi, bed sheets

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Smithtown
6.8 out of 10, (3 reviews)
"We enjoyed our stay. The apartment was simple, clean, and comfortable. The neighborhood felt safe, and it was easy to call Uber for rides. LIRR access was also convenient, which made traveling to New York City and Stony Brook very manageable. The highlight was the beautiful backyard, which made the place feel relaxing."
United States
Jing L.
The price is ￥23,821
￥35,066 total
includes taxes & fees
Feb 17 - Feb 18
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
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

Trumbull Marriott Shelton

Trumbull Marriott Shelton

10/10 Excellent
"Fast check in, nice staff ,plenty of parking gym,and pool,close to everything ."
Wilfredo 1-night trip
Posted 1 day ago
Trumbull Marriott Shelton

Find out more about Sheffield Island

Search for holiday rentals in Sheffield Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Sheffield Island using one of the methods below:

  • View our selection of featured holiday rentals in Sheffield Island
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Look no further and take a look at our great range of rental properties in Sheffield Island!

Frequently asked questions

Are there vacation rentals in Sheffield Island?

Yes, we have vacation rentals close to top sights in Sheffield Island, or you can go with a more remote option if you'd like a relaxing place to stay. Sheffield Island is known for its monuments.

What's the top vacation rental that Sheffield Island has to offer?

Beautiful historic home in Stony Brook!: This vacation home rental outside of Sheffield Island has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What’s there to see and do in Sheffield Island?

Explore the area and family-friendly sights such as Norwalk Maritime Aquarium, or get out into nature at a spot like Calf Pasture Beach. In the larger area, you’ll find Sheffield Island Lighthouse and The Maritime Aquarium.

What’s a vacation rental in Sheffield Island like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Sheffield Island. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a small group gathering.