Photo by Richard Miska

Sheffield Island Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Sheffield Island

Stamford Suites

4.0 star property
5.6 out of 10, (48)
"It was great relaxing stay"
The price is AU$267
includes taxes & fees
5 Aug - 6 Aug
Stamford Suites

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (63)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
The price is AU$456
includes taxes & fees
25 Aug - 26 Aug
Guesthouse at Norwalk Inn

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (31)
"This place a marvelous!! Very nice and clean!! The scenery of nature that I experienced when waking up was very refreshing!!"
Global Luxury Suites White Plains

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

2.0 out of 10, (1)
"We went to check in around 5pm since check in was at 4. Luckily we were able to leave our kids with family while we went to check out the place and unload our luggage. We arrived and parked in the street like we were told and walked to the back around the whole yard on an unfinished path. We had to step over a large roof drain pipe to get to the basement door which was not very safe. We went inside turned on the lights and proceeded to check the rooms to find the floors filthy, crumbs were all...
The price is AU$359
includes taxes & fees
31 Aug - 1 Sept
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

Business or Weekend escape

9.2 out of 10, Wonderful, (43)
"Very nice owner with great communication. "
The price is AU$229
includes taxes & fees
10 Aug - 11 Aug
Business or Weekend escape

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

9.0 out of 10, Wonderful, (7)
"This property is well maintained. Some amenities available that made our stay more enjoyable. My only issue was the amount of noise you could hear throughout the night.but once you're asleep it doesn't matter. "
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (16)
"The covered parking was really helpful on a cold day."
Luxury Apartments by Hyatus at The Asher

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

10.0 out of 10, Exceptional, (1)
"Lovely studio in downtown...despite being downtown. Owner was very receptive Studio had everything we needed such as sundry items...coffee pods, sugar, salt pepper and earplugs...to drown out the load seagulls. Short walk to the Ampitheater. Classic art deco buildings along the walk and quite few decent restaurants"
The price is AU$364
includes taxes & fees
10 Aug - 11 Aug
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

10.0 out of 10, Exceptional, (10)
"Super enjoyable."
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Waterfront Beautiful Fun Beach Cottage Sunsets Inspiring Peaceful 1hr NYC Wow

Modern House in Black Rock

2.0 star property
9.0 out of 10, Wonderful, (6)
"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

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (65)
"Great home to stay. Beautiful area to explore!"
The price is AU$826
includes taxes & fees
5 Aug - 6 Aug
Captain's Cottage - Cold Spring Harbor Water Views

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (5)
"Honestly i do not know where to start, everything was perfect. My friend and i needed a place to stay while celebrating a baby shower and this rental was not only the perfect location but it was a great price as well. The place was very clean, very roomy, had all the amenities we needed, and the host were very kind and attentive. This place checked all our boxes and we would absolutely stay here again next time we visit the Island. I highly recommend this rental to others!"
The price is AU$303
includes taxes & fees
2 Sept - 3 Sept
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Spacious One Bedroom suite

8.0 out of 10, Very good, (5)
"Nice stay enjoyed it "
Spacious One Bedroom suite

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

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is AU$491
includes taxes & fees
6 Aug - 7 Aug
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

10.0 out of 10, Exceptional, (21)
"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

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

The price is AU$312
includes taxes & fees
2 Sept - 3 Sept
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

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

10.0 out of 10, Exceptional, (1)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
The price is AU$2,159
includes taxes & fees
6 Aug - 7 Aug
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Soothing Carriage House with Hot Tub in charming Stratford

10.0 out of 10, Exceptional, (1)
"John was a wonderful Host.We had a very relaxing time in the Hot Tub and the carriage house had everything we needed for our stay.We will definitely book again,Lisa and Holly"
Soothing Carriage House with Hot Tub in charming Stratford
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sheffield Island Hotel Reviews

Frequently asked questions

Are there holiday rentals in Sheffield Island?

Yes, there are holiday rentals close to the most popular sights in Sheffield Island, or you can select a more secluded option if you're looking for a relaxing stay. Sheffield Island is known for its monuments.

What are some of the best holiday rentals that Sheffield Island has to offer?

Business or Weekend escape: This holiday home rental outside of Sheffield Island is equipped with a BBQ, air conditioning and WiFi 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 wider area, you’ll find Sheffield Island Lighthouse and The Maritime Aquarium.

What’s a holiday rental in Sheffield Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sheffield Island. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family gatherings.