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Compare 242 Vacation Homes in Sheffield Island with updated reviews, rates, and availability.

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (94)
"I cannot say enough good things about Deirdre's beautiful home and how grateful my family was to be able to stay here during our visit to Stamford. The house is perfect for a family with younger kids; they were so excited to have their very own play room! The rooms and bathrooms are well equipped with everything you might need, as was the kitchen. Deirdre in particular was so communicative and helpful with all of our questions. We very much hope to have an excuse to stay here again!"
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (14)
"We were in town for work for the week and found this site online. Great spot, nice a quiet. "
Historic Hideaway with Lake Access!

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

9.4 out of 10, Exceptional, (10)
"We were in town for work so didn't spend much time in the house but it was clean, convenient, easy parking, and a great value. "
The price is AED 735
AED 1,227 total
includes taxes & fees
4 Mar - 5 Mar
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

Cozy retreat with fenced in yard—centrally located in the heart of Long Island.

10.0 out of 10, Exceptional, (12)
"We had a wonderful stay at this property! The home was beautiful, well-maintained, and had everything we needed for a comfortable visit. The location was absolutely perfect—convenient to everything we needed to do in Huntington. The host was incredibly responsive and made sure we felt welcome from start to finish. We truly appreciated the attention to detail and would highly recommend this property to anyone looking for a great place to stay. We’d happily return in the future. "
Cozy retreat with fenced in yard—centrally located in the heart of Long Island.

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (54)
"Great location, very comfortable, nicely decorated, and well stocked re necessities. "
The price is AED 720
AED 1,498 total
includes taxes & fees
5 Mar - 6 Mar
Captain's Cottage - Cold Spring Harbor Water Views

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (18)
"This was a late holiday gathering of family members from St. Louis and Rye New York. Great and easy spot to get to. Pretty setting with the water view. I am sure in warmer seasons it be great spot for all the outside amenities. Six adults and one baby. Space nice set up. "
The price is AED 2,810
AED 4,743 total
includes taxes & fees
27 Mar - 28 Mar
Waterview House Walking Distance from Cove Beach

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (28)
"We had 8 people staying in the house. We were in town for a wedding. The house was well fitted for us. Kitchen had all the dishes we needed. Appliances all worked well. Nice walk to the sound. Neighborhood was kind of iffy but we had no problems. "
Cheerful 4 bedrooms residential house.

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (18)
"We were 9 adult women. There was plenty of space for us to gather as a group as well as sleep. The house is clean and in a great neighborhood. Very easy on and off to the highway to get to our conference in Darien. Highly recommend."
New Beach Home near Stamford Downtown/Shippan

Seaview Ave House-4BR/8PPL Retreat

9.8 out of 10, Exceptional, (8)
"This was an awesome place to stay. Very clean and well kept. When I needed to get in touch for some last minute questions, the owner was very prompt and eager to help. I would definitely stay here again."
Seaview Ave House-4BR/8PPL Retreat

Glen Cove Home: Walk to Boardwalk + Dining!

9.0 out of 10, Wonderful, (12)
"I enjoyed everything about this property except the description stated there were 2 steps to enter property. It failed to metro the 15 stairs once you opened the door. My aunt struggled with this so be aware when booking this property if you have accessibility needs. "
Glen Cove Home: Walk to Boardwalk + Dining!

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (6)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

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 731
AED 1,674 total
includes taxes & fees
4 Mar - 5 Mar
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

Cozy 3BR Near Huntington's Nightlife & Beach

2.0 star property
4.8 out of 10, (3)
"Situated just off the main street of Huntington, this comfy cottage is a terrific home base for exploring the north shore area. It has ample space: generous sitting room and kitchen with modern amenities, private office area, and 3 large bedrooms with lots of closet space. The beds are perfectly firm, pillows are plump and sheets are oh-so soft. The bathroom has some updates and delivers the basics such as nice shower pressure and new sink/vanity. Very clean and tidy, parts of the home still...
Cozy 3BR Near Huntington's Nightlife & Beach

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

10.0 out of 10, Exceptional, (12)
"I would recommend this property "
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

Entire House on Scenic Estate with Private Pond in Exclusive Neighborhood

9.8 out of 10, Exceptional, (12)
"The property is beautiful and relaxing! We had everything we needed for a great Thanksgiving. Gustavo was an excellent host who checked in on us for anything we might need. I highly recommend this rental! The pond view is stunning and we had 4 ducks visit. "
Entire House on Scenic Estate with Private Pond in Exclusive Neighborhood

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

Long Island Estate with Heated Pool 1 Hr from Manhattan

Long Island Estate with Heated Pool 1 Hr from Manhattan

Lovely Basement with 2 Bedrooms and Kitchen

10.0 out of 10, Exceptional, (14)
"3 of us shared this 2 bedroom basement apartment. Everything was clean and comfortable. There were nice touches of providing some coffee, cereal, snacks and even a half gallon of milk. There was plenty of street parking and the location was very convenient for our needs. I would stay there again. "
Lovely Basement with 2 Bedrooms and Kitchen

Stunning direct waterfront beach house!

10.0 out of 10, Exceptional, (6)
"My wife and I, our Son and his three teenagers had a wonderful week at this well appointed home right on the Beach! It was well outfitted with all the accomodations you could want for a great time. We have stayed at many Vrbo's, and most are run like a business, with limited supplies and accomodations. This property was supplied with everything as if it was our own place! Beach chairs, beach towels, fire pit with wood to burn, a fully equiped kitchen, extra suppliers, etc.The pictures are...
Stunning direct waterfront beach house!
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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Other property types in Sheffield Island

Global Luxury Suites White Plains

3.5 star property
7.0 out of 10, Good, (28)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains

Stamford Suites

3.0 star property
5.6 out of 10, (23)
"Room was very spacious "
The price is AED 621
AED 714 total
includes taxes & fees
16 Mar - 17 Mar
Stamford Suites

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (48)
"Excellent stay"
The price is AED 834
AED 1,161 total
includes taxes & fees
9 Mar - 10 Mar
DUNE Fairfield Beach
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.