Photo by Richard Miska

Sheffield Island holiday rentals

We found 304 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Sheffield Island to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for hanging out with the people that matter most, such as Wi-Fi and cable TV. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Take in the waterfront beauty of Sheffield Island

Enjoy the monuments and other features of Sheffield Island. One of the city's many top draws is its island views. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Sheffield Island

Are you looking for things to do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Sheffield Island has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Norwalk Maritime Aquarium (3.4 mi / 5.4 km)
  • Chelsea Piers (5.1 mi / 8.2 km)
  • Del Vino Vineyards (10.7 mi / 17.2 km)
  • Bayville Adventure Park (13.1 mi / 21.1 km)
  • Cold Spring Harbor Laboratory (13.5 mi / 21.7 km)
  • Rye Playland (14.6 mi / 23.5 km)

Exploring the natural features in Sheffield Island

Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Sheffield Island. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Calf Pasture Beach (2.8 mi / 4.5 km)
  • Cove Island Park (4.4 mi / 7 km)
  • Compo Beach (4.9 mi / 7.9 km)
  • West Beach (5.6 mi / 9 km)
  • Greenwich Point Park (9.2 mi / 14.9 km)
  • Caumsett State Historic Park Preserve (9.5 mi / 15.3 km)

Travelling to and around Sheffield Island

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 15 mi (24.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), which is 16.7 mi (26.9 km) away.

Frequently asked questions

What is the best area to stay in Sheffield Island when booking a holiday rental?
When considering a holiday rental in Sheffield Island, Connecticut, a popular area to stay is near the waterfront. This picturesque location offers stunning views of Long Island Sound and provides easy access to a variety of outdoor activities. The area is known for its tranquil atmosphere and scenic walking paths, making it a delightful spot for those looking to unwind.Nearby attractions include the Sheffield Island Lighthouse, which is a charming historical site and often offers tours during the warmer months, allowing visitors to appreciate the maritime heritage of the region. Additionally, the expansive Calf Pasture Beach is a popular destination for both locals and visitors alike, featuring picnic areas, sandy shores, and recreational opportunities such as swimming and beach sports.In terms of holiday rentals, the waterfront area boasts a good selection of properties, ranging from quaint cottages to more spacious homes, suiting various group sizes and preferences.
What are the top attractions in Sheffield Island?
In Sheffield Island, Connecticut, visitors can enjoy a tranquil escape surrounded by natural beauty and maritime history. One of the top attractions is the Sheffield Island Lighthouse, which offers guided tours and stunning views of Long Island Sound. The island is accessible by ferry, providing a scenic journey that adds to the experience.Additionally, the nearby Norwalk Islands provide opportunities for kayaking and birdwatching, making it a haven for nature enthusiasts. The surrounding waters are superb for fishing and boating, while the beaches offer a relaxing spot to unwind. For those interested in local culture, the Norwalk Maritime Aquarium is just a short distance away, showcasing marine life native to the region and providing educational exhibits.
Are all fees included in the Sheffield Island holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Sheffield Island holiday homes with parking?
Stayz offers a wide selection of holiday homes in Sheffield Island with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Sheffield Island holiday homes?
You can find great discounts on holiday homes in Sheffield Island on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Sheffield Island holiday home booking on Stayz?
To find Sheffield Island holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Sheffield Island?
A long-stay holiday home in Sheffield Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Sheffield Island holiday home?
Book your Sheffield Island holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Sheffield Island?
Prices for holiday homes in Sheffield Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Sheffield Island to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.