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Compare 298 Vacation Homes in Sheffield Island with updated reviews, rates, and availability.

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (97)
"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!

Business or Weekend escape

9.6 out of 10, Exceptional, (36)
"Very nice owner with great communication. "
The price is AED 275
AED 496 total
includes taxes & fees
1 Jun - 2 Jun
Business or Weekend escape

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

The price is AED 643
AED 891 total
includes taxes & fees
1 Jun - 2 Jun
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!

9.6 out of 10, Exceptional, (5)
"Very nice place close to the beach and nice restaurant. The host was very nice and did a very good banana cake."
Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!

Beautiful Pound Ridge with a pool

Beautiful Pound Ridge with a pool

3-bedroom house in pleasant Norwalk with Pool, outdoor BBQ, and so much more

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay. "
3-bedroom house in pleasant Norwalk with Pool, outdoor BBQ, and so much more

Quaint duplex with private yard. Walk to beach, dining, & shopping!

10.0 out of 10, Exceptional, (40)
"The unit is just as described, and the owner is very, friendly and responsive would definitely stay here again"
Quaint duplex with private yard. Walk to beach, dining, & shopping!

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

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

10.0 out of 10, Exceptional, (1)
"Perfect setting for our family as we celebrated a college graduation locally. Great location. Home has many amenities and you cannot beat lake living! Trying to think about a reason we can return. ;-)"
Lake house cozy to relax with a family. 6 bedroom very spacious house.

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

Spacious Gorgeous Getaway perfect for family reunion or business

9.6 out of 10, Exceptional, (7)
"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

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

Modern 3 Bed House in Black Rock

2.0 star property
"Home was as advertised "
Modern 3 Bed House in Black Rock

Modern House in Black Rock

2.0 star property
9.2 out of 10, Wonderful, (5)
"Very easy stay and great location convenient to Fairfield University . Plenty of options to walk to for coffee or meals. Had everything we needed. Clean, well equipped. Great communication with owners. "
Modern House in Black Rock

Charming 2-bedroom house with WiFi, AC in Fairfield

The price is AED 606
AED 1,347 total
includes taxes & fees
2 Jun - 3 Jun
Charming 2-bedroom house with WiFi, AC in Fairfield

GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

10.0 out of 10, Exceptional, (19)
"This house is amazing and location on a tributary to the Long Island sound is incredibly scenic. We'd absolutely stay again!"
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

Beautiful historic home in Stony Brook!

2.0 star property
8.6 out of 10, Excellent, (8)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!

Ultra-Modern Luxe - Sleek & Stunning Stay!

2.0 out of 10, (1)
"Do not work with this owner. They never sent us the check in information. When we contacted them they did not respond. When we finally spoke to them on the day of the rental they told us that there were wiring issues and a CO2 leak and told us to cancel the reservation. We tried to cancel but as it was within 24 hours we were not able to. They finally told us 1 hour before check-in time the rental was in fact ok. By then we already had checked into a hotel. They refused to cancel the...
Ultra-Modern Luxe - Sleek & Stunning Stay!

Beautiful Waterfront Sunset Beach House Oasis Walk to Village Beaches 1hr NYC

10.0 out of 10, Exceptional, (5)
"Perfect location to enjoy Northport! Everything is within walking distance. Host was very helpful and accommodating. Great stay and will definitely return! "
Beautiful Waterfront Sunset Beach House Oasis Walk to Village Beaches 1hr NYC

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!
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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