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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 300 Vacation Homes in Sheffield Island with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard
Dining

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (9)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard
Captain's Cottage - Cold Spring Harbor Water Views
Aerial view

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (59)
"Everything was awesome! Would definitely stay here again! "
The price is AED 845
AED 1,872 total
includes taxes & fees
20 May - 21 May
Captain's Cottage - Cold Spring Harbor Water Views
Business or Weekend escape
Pool

Business or Weekend escape

9.6 out of 10, Exceptional, (34)
"Very nice owner with great communication. "
The price is AED 275
AED 496 total
includes taxes & fees
12 May - 13 May
Business or Weekend escape
Cheerful 4 bedrooms residential house.
Fridge, microwave, dishwasher, coffee/tea maker

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (30)
"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.
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Fridge, microwave, oven, stovetop

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"Very convenient and plenty of room. Easy to get to NY from Stamford train station and everything we needed nearby."
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Main Street Westport, walk to shops, dining, downtown
Miscellaneous

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Beach nearby, beach towels

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (32)
"The house was in a great location, was well-stocked and clean, and the host was very responsive. Would definitely stay here again and highly recommend. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Over Sized Colonial on Private Road.
Exterior

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"We were a family of 4 adults and 2 toddlers staying over Thanksgiving. We really didn’t need all the space but we certainly enjoyed it. There’s a huge well stocked kitchen, kids’ play areas on both the main floor and basement, and the property is massive and gorgeous. Great stay!"
Over Sized Colonial on Private Road.
New Beach Home near Stamford Downtown/Shippan
Terrace/patio

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"We had a great time and it was a very spacious and clean location "
The price is AED 2,182
AED 3,980 total
includes taxes & fees
20 May - 21 May
New Beach Home near Stamford Downtown/Shippan
Glen Cove Home: Walk to Boardwalk + Dining!
Fridge, microwave, stovetop, dishwasher

Glen Cove Home: Walk to Boardwalk + Dining!

9.2 out of 10, Wonderful, (15)
"We enjoyed staying here for a long weekend while touring maritime colleges in the area. This nice quiet neighborhood was restful at the end of each day and convenient to everywhere we needed to be. The nearby brewery on the harbor was a great spot for lunch."
Glen Cove Home: Walk to Boardwalk + Dining!
Westport Gem - walk to shops, dining, town center, pet-friendly
Miscellaneous

Westport Gem - walk to shops, dining, town center, pet-friendly

10.0 out of 10, Exceptional, (3)
"Had a great time! My favorite part was sitting on the back deck w coffee in the morning. There were so many birds and the tall hedges that protected the privacy was so charming. The host was so nice and left out fruit and snacks. Loved staying there!"
Westport Gem - walk to shops, dining, town center, pet-friendly
Spacious Gorgeous Getaway perfect for family reunion or business
Fridge, microwave, oven, stovetop

Spacious Gorgeous Getaway perfect for family reunion or business

9.8 out of 10, Exceptional, (6)
"House was perfect for the group. We had everything we needed and plenty of room for us. Owner was great with communications before and during our stay"
Spacious Gorgeous Getaway perfect for family reunion or business
Charming Mamaroneck Home ~ 22 Mi to Manhattan
TV

Charming Mamaroneck Home ~ 22 Mi to Manhattan

7.8 out of 10, Good, (12)
"Clean and easy check in--Great Location!"
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Breathtaking Waterfront house
Outdoor pool

Breathtaking Waterfront house

9.4 out of 10, Exceptional, (3)
"Fun property, kitchen needs a little organizing, And instructions for tv and remotes would be helpful"
Breathtaking Waterfront house
Cozy retreat with fenced in yard—centrally located in the heart of Long Island.
Sun loungers, beach towels

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

10.0 out of 10, Exceptional, (12)
"Clean, cozy and would stay again."
Cozy retreat with fenced in yard—centrally located in the heart of Long Island.
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS
Outdoor dining

GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

10.0 out of 10, Exceptional, (19)
"What a wonderful place to get the family all together. House was perfect. We enjoyed the spacious accommodations and it was very well equipped! We would highly recommend this home! "
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS
Akasa Ocean Front Oasis- Seasonal Pool, Grill
Interior

Akasa Ocean Front Oasis- Seasonal Pool, Grill

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great property with a bunch of space and great amenities and location. "
Akasa Ocean Front Oasis- Seasonal Pool, Grill
Historic Hideaway with Lake Access!
Fridge, microwave, oven, stovetop

Historic Hideaway with Lake Access!

9.8 out of 10, Exceptional, (16)
"We were in town for work for the week and found this site online. Great spot, nice a quiet. "
Historic Hideaway with Lake Access!
Waterview House Walking Distance from Cove Beach
TV, fireplace, books, stereo

Waterview House Walking Distance from Cove Beach

9.2 out of 10, Wonderful, (19)
"Easy entrance and exit policy. Great communication from owners. Perfect location. "
The price is AED 1,469
AED 3,067 total
includes taxes & fees
20 May - 21 May
Waterview House Walking Distance from Cove Beach
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Aerial view

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

10.0 out of 10, Exceptional, (15)
"Super clean, love the decor and great communication with home owner. Highly recommend!"
The price is AED 797
AED 1,926 total
includes taxes & fees
26 May - 27 May
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
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

Stamford Suites
Exterior

Stamford Suites

3.0 star property
6.0 out of 10, (29)
"Convenience. Full kitchen and spacious rooms"
The price is AED 650
AED 748 total
includes taxes & fees
11 May - 12 May
Stamford Suites
DUNE Fairfield Beach
Private beach nearby, sun loungers, beach umbrellas, beach towels

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (52)
"Absolutely perfect location for visiting Fairfield University! Everything about it exceeded our expectations."
The price is AED 793
AED 1,114 total
includes taxes & fees
12 May - 13 May
DUNE Fairfield Beach
Global Luxury Suites White Plains
Reception

Global Luxury Suites White Plains

3.5 star property
6.6 out of 10, (30)
"Nice view from the apartment and great for business trip. "
Global Luxury Suites White Plains
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.