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Sheffield Island Vacation Rentals

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Check prices for these dates

Tonight
Jun 25 - Jun 26
Tomorrow
Jun 26 - Jun 27
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Sheffield Island

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beach
Smart TV, fireplace, offices

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beach

10.0 out of 10, Exceptional, (1)
"Very comfortable and welcoming Only problem was only one bathroom door closed the other one appeared to be in disrepair Other then that all was well"
The price is ￥51,308
￥97,461 total
includes taxes & fees
Jul 16 - Jul 17
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beach
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Private kitchen

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

The price is ￥22,611
￥33,284 total
includes taxes & fees
Jul 1 - Jul 2
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Business or Weekend escape
Pool

Business or Weekend escape

9.6 out of 10, Exceptional, (37)
"Very nice owner with great communication. "
The price is ￥12,320
￥21,234 total
includes taxes & fees
Jun 30 - Jul 1
Business or Weekend escape
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Outdoor pool, a heated pool

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

10.0 out of 10, Exceptional, (6)
"the place was amazing and the best house we have seen. definitely gonna come again"
The price is ￥144,306
￥226,217 total
includes taxes & fees
Jun 26 - Jun 27
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Amazingly Cozy Comfort Downtwn, Amphitheater, 2 min ferry & train station
In-room safe, iron/ironing board, free WiFi, bed sheets

Amazingly Cozy Comfort Downtwn, Amphitheater, 2 min ferry & train station

10.0 out of 10, Exceptional, (1)
"Great experience. Very close to a lot of downtown restaurants and Bridgeton. 10 to 15 mnutes from the beach. Lots of added special touches and amenities. Great job by the host."
The price is ￥14,494
￥26,234 total
includes taxes & fees
Jul 7 - Jul 8
Amazingly Cozy Comfort Downtwn, Amphitheater, 2 min ferry & train station
The B&W Haven 5BR Home with yard theater + Office
Fridge, microwave, oven, stovetop

The B&W Haven 5BR Home with yard theater + Office

9.2 out of 10, Wonderful, (7)
"The property was clean, well equipped and had good off street parking. Andrew was responsive and helpful. Definitely recommend. "
The price is ￥38,923
￥95,392 total
includes taxes & fees
Jun 26 - Jun 27
The B&W Haven 5BR Home with yard theater + Office
Upscale 4BR Retreat at the Reservoir!
Fridge, microwave, oven, stovetop

Upscale 4BR Retreat at the Reservoir!

The price is ￥76,528
￥127,866 total
includes taxes & fees
Jul 23 - Jul 24
Upscale 4BR Retreat at the Reservoir!
Charming Long Island Family Getaway with Pool. An hour from Hamptons
Pool

Charming Long Island Family Getaway with Pool. An hour from Hamptons

7.0 out of 10, Good, (6)
"Had a great time here. The house was clean and well maintained. The host communicated with us often and overall it was a great stay!"
The price is ￥128,127
￥242,930 total
includes taxes & fees
Jul 20 - Jul 21
Charming Long Island Family Getaway with Pool. An hour from Hamptons
Centric property close to all the great things in the city
Fridge, oven, stovetop, coffee/tea maker

Centric property close to all the great things in the city

8.2 out of 10, Very Good, (12)
"This rental was great accommodation"
The price is ￥25,365
￥46,744 total
includes taxes & fees
Jul 6 - Jul 7
Centric property close to all the great things in the city
Modern + Spacious 5BR/2BA Home, Renovated Backyard
5 bedrooms, desk, iron/ironing board, free WiFi

Modern + Spacious 5BR/2BA Home, Renovated Backyard

9.0 out of 10, Wonderful, (2)
"Great house! Excellent owners! Everything was perfect. Very much appreciated the attentiveness of the owners and how quick they were to respond to our questions. Despite that the area looks to be less than desirable, we were extremely comfortable and very much enjoyed ourselves. Also, the amenities were amazing - stayed during a heat wave, but the ACs provided the right amount of relief, so we all slept well. "
Modern + Spacious 5BR/2BA Home, Renovated Backyard
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!
Interior

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

The price is ￥115,952
￥215,453 total
includes taxes & fees
Jul 5 - Jul 6
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!
Charming 2-bedroom house with WiFi, AC in Fairfield
Interior

Charming 2-bedroom house with WiFi, AC in Fairfield

10.0 out of 10, Exceptional, (1)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is ￥21,524
￥50,408 total
includes taxes & fees
Jun 30 - Jul 1
Charming 2-bedroom house with WiFi, AC in Fairfield
Marine Theme - 4 BR - Backyard - Fire pit
Fridge, microwave, oven, stovetop

Marine Theme - 4 BR - Backyard - Fire pit

9.8 out of 10, Exceptional, (6)
"Had a great stay at Sarah’s place. She was very communicative and helpful before and during our stay. The house was nice and large - it was great having two living rooms for our large group. Convenient location close to many stores and sights!"
The price is ￥35,561
￥76,949 total
includes taxes & fees
Jul 7 - Jul 8
Marine Theme - 4 BR - Backyard - Fire pit
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Outdoor dining

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

10.0 out of 10, Exceptional, (17)
"Super clean, love the decor and great communication with home owner. Highly recommend!"
The price is ￥60,440
￥113,679 total
includes taxes & fees
Jun 29 - Jun 30
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
Bright Escape, Top-Rated Design, Fire pit, Near Beach, 90 minutes to NYC
Fridge, microwave, oven, stovetop

Bright Escape, Top-Rated Design, Fire pit, Near Beach, 90 minutes to NYC

10.0 out of 10, Exceptional, (5)
"And the bed was confortable"
The price is ￥41,293
￥90,354 total
includes taxes & fees
Jun 26 - Jun 27
Bright Escape, Top-Rated Design, Fire pit, Near Beach, 90 minutes to NYC
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Coffee/tea maker, spices

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

10.0 out of 10, Exceptional, (3)
"Great space! Very clean & well appointed! If you forgot to pack it, it is probably there!"
The price is ￥29,912
￥57,679 total
includes taxes & fees
Jun 30 - Jul 1
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Terrace/patio

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

The price is ￥15,175
￥24,840 total
includes taxes & fees
Jul 21 - Jul 22
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town
Pool

Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

The price is ￥253,645
￥353,436 total
includes taxes & fees
Jul 2 - Jul 3
Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Exterior

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
The price is ￥63,471
￥118,304 total
includes taxes & fees
Jun 30 - Jul 1
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Captain's Cottage - Cold Spring Harbor Water Views
Smart TV, fireplace, table tennis, computer monitors

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (61)
"Great home to stay. Beautiful area to explore!"
The price is ￥52,903
￥99,358 total
includes taxes & fees
Jul 9 - Jul 10
Captain's Cottage - Cold Spring Harbor Water Views
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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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?

Business or Weekend escape: This vacation home rental outside of Sheffield Island is equipped with a barbecue grill, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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.