Photo by Richard Miska

Search Vacation Homes in Sheffield Island

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare Vacation Homes in Sheffield Island with updated reviews, rates, and availability.

Business or Weekend escape
A Queen Size Bed for Two Persons and Also Queen Size Sofa Bed for Two Persons.

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AED 294
AED 517 total
includes taxes & fees
1 Jan - 2 January 2025
Business or Weekend escape
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Exterior

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (115)
"Enjoyed the theater room and the comfortable bed"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa
Living area

Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa

10.0 out of 10, Exceptional, (10)
"This home is charming and what a surprise to see a Christmas tree set up! Our family spent Thanksgiving at this perfectly updated home. The home was very clean, functional and the kitchen was well stocked. I would not hesitate to recommend this home."
The price is AED 657
AED 1,713 total
includes taxes & fees
27 Jan - 28 January 2025
Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa
Cheerful 4 bedrooms residential house.
Exterior

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (25)
"Great communication and accommodations from the host. We were in town for a concert and the location couldn't have been better! Would recommend this stay for anyone looking within the area."
Cheerful 4 bedrooms residential house.
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Living area

Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

9.4 out of 10, Exceptional, (8)
"Space was nice. Need top sheets on beds. Noisy location and basement tenant."
The price is AED 1,102
AED 1,653 total
includes taxes & fees
2 Jan - 3 January 2025
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (62)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Waterview House Walking Distance from Cove Beach
Sunbathing lounge chairs

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (16)
"The house is beautiful, amazing views! Communication was punctual."
The price is AED 1,866
AED 3,687 total
includes taxes & fees
16 Jan - 17 January 2025
Waterview House Walking Distance from Cove Beach
New Beach Home near Stamford Downtown/Shippan
Open concept living/dining room

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (16)
"Exactly as advertised, great location, easy check-in, hosts responded immediately to questions. Recommended."
The price is AED 2,005
AED 3,891 total
includes taxes & fees
30 Dec - 31 Dec
New Beach Home near Stamford Downtown/Shippan
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Dining

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Captain's Cottage - Cold Spring Harbor Water Views
View Cold Spring Harbor in the Fall

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (53)
"Cute, well-appointed house, great communication, fun stay!"
The price is AED 735
AED 1,539 total
includes taxes & fees
7 Jan - 8 January 2025
Captain's Cottage - Cold Spring Harbor Water Views
Elegant private resort style North Shore home
Outdoor dining

Elegant private resort style North Shore home

9.6 out of 10, Exceptional, (17)
"Super easy process. The house is beautiful and very clean. I’m super picky when it comes to cleanliness where I stay. This place is aces. "
Elegant private resort style North Shore home
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
Living area

Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

9.2 out of 10, Wonderful, (5)
"It’s nice to have a place for our family of 5 that actually fits us all. Plenty of space and very clean. Thanks "
The price is AED 845
AED 1,816 total
includes taxes & fees
7 Jan - 8 January 2025
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
Charming duplex with private yard. Close to the beach, dining & shopping!
Living area

Charming duplex with private yard. Close to the beach, dining & shopping!

9.8 out of 10, Exceptional, (36)
"Duplex unit was clean, as described and perfect for our stay visiting family in Rye. Lots of extra towels and nice welcoming snacks in the kitchen. Super convenient location. Will likely stay there again. "
Charming duplex with private yard. Close to the beach, dining & shopping!
Historic Hideaway with Lake Access!
Living area

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (12)
"Overall, very nice historic home. Very clean, perfect location for our family holiday, wonderful mattresses on all beds, well stocked kitchen with all cooking necessities. Good communication with owners who promptly helped to rectify a few issues. Would recommend to anyone looking to stay in this area."
Historic Hideaway with Lake Access!
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
Modern mid century guest house. Built in 1955 inside of old court

ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home

10.0 out of 10, Exceptional, (24)
"Pre-stay communication was excellent, with our host contacting me with suggestions for outings (I asked). Our host met us, gave us a tour of the property - not just the living space but the grounds, too. The house is cozy, well thought out and has small touches like a deck of cards (in case you have a couple of minutes of downtime), a beautiful tea set with a variety of delicious teas to use. The house is thoughtfully decorated, the couch and bed are comfortable and there is plenty of space for...
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
Private Luxury Stay in Expansive Home & Property
Exterior

Private Luxury Stay in Expansive Home & Property

9.0 out of 10, Wonderful, (2)
"Good times"
Private Luxury Stay in Expansive Home & Property
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
Exterior

Private Renovated Home Convenient to Sacred Heart & Fairfield Universities

10.0 out of 10, Exceptional, (26)
"Jon is an excellent and very responsive host. His home is beautiful, very clean, well appointed, and organized. All the comforts of home are provided. This is our second time staying at this property and we will be back!"
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
Beautiful downstairs apartment. Walk to town, train, & beach ferry!
Outdoor dining

Beautiful downstairs apartment. Walk to town, train, & beach ferry!

10.0 out of 10, Exceptional, (18)
"We had a wonderful day. The location is fantastic with easy access to restaurants and the rest of Greenwich. The place itself is well appointed and in good shape. We would absolutely stay here again. Loved it. (neighbors upstairs stomp around a bit!)"
Beautiful downstairs apartment. Walk to town, train, & beach ferry!
Spacious 3b/3b Mediterranean in White Plains
Living Room

Spacious 3b/3b Mediterranean in White Plains

9.6 out of 10, Exceptional, (10)
"Very beautiful and spacious home. Super clean and amenities galore. Quiet and peaceful neighborhood. Very well kept and loved the white picket fence. Felt very safe."
Spacious 3b/3b Mediterranean in White Plains
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train
Exterior

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

10.0 out of 10, Exceptional, (11)
"This was our 2nd stay and everything was fantastic once again! Highly recommended!!"
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train
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.
Don't see what you're looking for?
See all available properties in Sheffield Island
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Sheffield Island

Stamford Suites
Property amenity

Stamford Suites

2.5 star property
6.8 out of 10, (772)
"It was in walking distance of the event we were going to."
The price is AED 515
AED 592 total
includes taxes & fees
2 Jan - 3 January 2025
Stamford Suites
DUNE Fairfield Beach
Room

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (45)
"The property is generally old, but it was a nice renovation. Of the room. "
The price is AED 838
AED 1,166 total
includes taxes & fees
5 Jan - 6 January 2025
DUNE Fairfield Beach
Business or Weekend escape
A Queen Size Bed for Two Persons and Also Queen Size Sofa Bed for Two Persons.

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AED 294
AED 517 total
includes taxes & fees
1 Jan - 2 January 2025
Business or Weekend escape
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.