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Sheffield Island Holiday Rentals

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Our top choices for Sheffield Island holiday rentals

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (13 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is NZ$400
includes taxes & fees
13 July - 14 July
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Elite room stay

Elite room stay
Bridgeport
The price is NZ$592
includes taxes & fees
3 July - 4 July
Elite room stay

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (96 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is NZ$493
includes taxes & fees
5 July - 6 July
DUNE Fairfield Beach

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (55 reviews)
"I love the layout of this apt. Perfect for 2 to 3 people, it was clean and nothing out of place. The host was great and communicated well. I will be looking for this place again next year."
United States
Shamel
The price is NZ$258
includes taxes & fees
10 July - 11 July
Business or Weekend escape

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is NZ$574
includes taxes & fees
7 July - 8 July
Stamford Hideaway w/ Fire Pit

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (41 reviews)
"The location is beautiful and the hosts very amenable. Everything was clean, tidy and welcoming and there is a beautiful view out one of the bedroom windows to the lake in the back. I can highly recommend this destination and look forward to staying here again on a return trip!"
United States
Anonymous traveller
The price is NZ$601
includes taxes & fees
14 July - 15 July
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (16 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is NZ$718
includes taxes & fees
6 July - 7 July
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
7.2 out of 10, Good, (15 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is NZ$466
includes taxes & fees
13 July - 14 July
Centric property close to all the great things in the city

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
10.0 out of 10, Exceptional, (1 review)
"This hidden gem was a great find!!!! We went to a concert at the Hartford Healthcare Bridgeport Amphitheater and did not want to make the hour plus drive home. We were lucky to find this cute place to stay. It is a basement kitchen, living room ,2 bedroom establishment that is nicely put together and is super clean. We would choose to stay there again if we are in the neighborhood."
United States
Heidi M.
The price is NZ$514
includes taxes & fees
6 July - 7 July
Zen, Spacious & Comfy 2 bed, Lux beds

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (31 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is NZ$729
includes taxes & fees
5 July - 6 July
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is NZ$547
includes taxes & fees
13 July - 14 July
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is NZ$249
includes taxes & fees
6 July - 7 July
2-bedroom apartmet No cleaning Fee

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is NZ$342
includes taxes & fees
13 July - 14 July
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
The price is NZ$469
includes taxes & fees
16 July - 17 July
Stylish Home With Free ParkingZA

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is NZ$694
includes taxes & fees
8 July - 9 July
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

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

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (8 reviews)
"The Orange & Groovy Apt. was as described. All the amenities we needed and we had a lovely time and enjoyed the area. Will book again!"
United States
Betty W.
The price is NZ$405
includes taxes & fees
4 July - 5 July
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is NZ$736
includes taxes & fees
10 July - 11 July
Modern Luxe 1BR Apt in Downtown Stamford

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is NZ$678
includes taxes & fees
29 July - 30 July
Luxe Provincial Style Studio w/ Patio & Parking

Romantic Hide Out

Romantic Hide Out
Waterside
3.0 out of 10, (2 reviews)
"Check-in was at 3 PM and I was unable to reach the host until 11 PM that night to gain access to the property. They never sent anything in advance. It was the most miserable experience I have ever had."
United States
Cheryl H.
The price is NZ$449
includes taxes & fees
9 July - 10 July
Romantic Hide Out

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveller
The price is NZ$625
includes taxes & fees
7 July - 8 July
Renovated 2BR Retreat / Modern Comforts Included
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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Top Sheffield Island Hotel Reviews

Find out more about Sheffield Island

Everything you need to know about Sheffield Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sheffield Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sheffield Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sheffield Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sheffield Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sheffield Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheffield Island holiday rentals we have selected for you start as low as NZ$258 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sheffield Island rentals

At Expedia, we put the best Sheffield Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sheffield Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sheffield Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sheffield Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of Sheffield Island is equipped with a garden, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Rowayton Dog Park. In the wider area, you’ll find Sheffield Island Lighthouse and Calf Pasture Beach.

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.