Sag Harbor holiday lettings

We found 2,533 holiday rentals — enter your dates for availability

Discover a selection of 315 homes, 14 apartments and other holiday rentals in Sag Harbor that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you expect for your stay, which might include air conditioning and a pool. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Sag Harbor

Showing deals for:30 Jan - 6 Feb

Image gallery for Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

Exterior
10 out of 10, Exceptional, (112 reviews)
Exceptional
(112 reviews)

Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

Wainscott, NY

7% off
Price is £5,484
for 7 nights, 1 room
£783 per night
includes taxes & fees
Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

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Why visit Sag Harbor

  • Beautiful beaches: Spend leisurely days on the stunning beaches, perfect for sunbathing and family fun.
  • Charming marinas: Explore the picturesque marinas, ideal for boating and enjoying waterfront views.
  • Historic buildings: Discover the rich history of Sag Harbor through its well-preserved historic architecture.
  • Local culture: Immerse yourself in the vibrant local culture with unique shops and delightful eateries.
  • Accommodation variety: Choose from an array of charming cottages, private homes, and modern apartments for a perfect stay.

Popular types of accommodation in Sag Harbor

You've chosen Sag Harbor for your next getaway, and now it's time to select the perfect accommodation. Discover a range of delightful options, from private holiday homes and charming cottages to modern apartments. With various sag harbor rentals available, you're sure to find the ideal place to unwind and enjoy your holiday. Start exploring the best holiday rentals Sag Harbor has to offer for a truly memorable stay.

  • Houses: The most sought-after choice for holiday stays in Sag Harbor, offering spacious and comfortable accommodation for families or groups.
  • Cottages: A charming second option, these quaint retreats provide a homely atmosphere, perfect for a peaceful getaway.
  • Apartments: The third choice, ideal for couples or solo travellers, offering convenience in the heart of Sag Harbor.
  • Condos: A popular fourth option, combining modern amenities with lovely views for a delightful holiday experience.
  • Villas: The fifth choice, providing luxurious and spacious living for those seeking a more upscale stay.**

Top attractions in and around Sag Harbor

Sag Harbor is an idyllic destination for outdoor enthusiasts and romantic getaways, featuring a blend of beautiful beaches, historic buildings, and charming marinas. Visitors can immerse themselves in local culture while enjoying family-friendly activities. With various attractions to explore, Sag Harbor promises a delightful holiday experience for all types of travellers.

  • Sag Harbor Marine Park: A picturesque marina brimming with outdoor adventure opportunities. Enjoy kayaking, paddle boarding, or simply relax on the beach while soaking up the vibrant atmosphere of this charming coastal locale.
  • East Hampton Main Beach: Located 4.3km from Sag Harbor, this stunning beach offers golden sands and crystal-clear waters, perfect for sunbathing and swimming. The serene environment makes it a fantastic spot for a leisurely day by the sea.
  • Sag Harbor Whaling and Historical Museum: Delve into the rich maritime history of Sag Harbor at this local museum. Exhibits highlight the town's whaling past and cultural heritage, providing a captivating insight into the region's legacy.

Things to do recommended for couples

For a romantic getaway in Sag Harbor, indulge in a wine tasting at Wolffer Estates Vineyard, only 2.5km away. Enjoy a fun round of mini golf at Shelter Island Whale's Tail, 3.7km distant, and savour a lovely meal at Indian Wells Beach, 5.0km from the town.

Things to do recommended for families

Families will love exploring Cedar Point County Park, a serene recreational area just 2.5km from Sag Harbor, or enjoying the outdoor fun at the Greenport Carousel, located 5.0km away. Additionally, Kaplan Meadows Sanctuary offers another relaxing experience only 5.0km from Sag Harbor.

Things to do recommended for groups

Group travellers in Sag Harbor can enjoy a captivating performance at the Bay Street Theatre, indulge in a round of golf at Noyac Golf Club, and explore unique finds at The Style Bar, all while soaking up the charming atmosphere of this picturesque coastal town.

What do I need to keep in mind when booking a vacation in 'Sag Harbor

When you're planning a trip, whether it’s with a group, family, pets, or for an extended stay, be sure to narrow down your options according to your most important preferences. Here are some helpful booking tips for using Vrbo.

  • Traveling to Sag Harbor with a group: Think about how many bedrooms you will require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Sag Harbor with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Sag Harbor: For many, a family holiday isn't truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly options offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Sag Harbor: If you're in search of holiday rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Sag Harbor

Sag Harbor offers a delightful blend of outdoor adventures and romantic getaways, perfect for families seeking a memorable holiday. Spend your summer days lounging on beautiful beaches or exploring charming local shops and eateries. Nearby regions boast stunning scenery and luxury accommodations, ensuring a relaxing experience for all. Whether you fancy a beach house retreat or exciting excursions, Sag Harbor is an ideal destination for your next vacation in the United States.

  • Hamptons: The Hamptons, located a mere 3.1km from Sag Harbor, is a quintessential seaside destination renowned for its stunning beaches and vibrant outdoor experiences. Visitors are drawn to its charming coastal villages, world-class golf courses, and lively music concerts. The area boasts beautiful local landmarks, including pristine beaches and tranquil lakes, ideal for family outings and romantic strolls. The Hamptons offers a relaxed yet sophisticated atmosphere, making it a perfect spot for both adventure seekers and those looking to unwind.
  • East Hampton: Just 3.7km from Sag Harbor, East Hampton is a delightful city celebrated for its beautiful beaches and lush parks. A popular choice for outdoor enthusiasts, it offers a variety of recreational activities, including skiing and ample green spaces for leisurely picnics. The area’s charming family beaches provide a perfect setting for relaxation, while the local parks invite exploration and nature walks. East Hampton’s combination of natural beauty and community spirit makes it an inviting destination for couples and families alike.
  • Bridgehampton: Located only 2.5km from Sag Harbor, Bridgehampton is a charming city that captures the essence of beachside living. Known for its stunning shoreline and outdoor recreation, visitors can enjoy the thrill of skiing at nearby resorts or bask in the sun on family-friendly beaches. With picturesque lakes and a welcoming atmosphere, Bridgehampton is ideal for those seeking a romantic getaway or a fun-filled family holiday. The area's blend of scenic beauty and engaging activities makes it a must-visit during your stay in Sag Harbor.

Best time to go to Sag Harbor

If you're planning a trip to Sag Harbor, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyAverageModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyModerately HighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyModerately HighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyModerately HighModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyModerately LowAverage
November49.6°F (9.8°C)Light RainMostly SunnyModerately LowAverage
December42.1°F (5.6°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides you with a convenient platform to plan new holidays, refine your arrangements, or manage your bookings with ease. The properties you've saved or reserved are thoughtfully categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Sag Harbor

Enjoy the churches and other features of Sag Harbor. This city's boating, island views and beaches draw many visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Sag Harbor

Are you searching for top things to see and do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Sag Harbor has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Wolffer Estates Vineyard (3.7 mi / 6 km)
  • Noyac Golf Club (4 mi / 6.4 km)
  • LongHouse Reserve (5 mi / 8 km)
  • Duck Walk Vineyards (7.6 mi / 12.3 km)
  • Kontokosta Winery (8.9 mi / 14.4 km)
  • Raphael Winery (9.1 mi / 14.7 km)

Exploring the natural features in Sag Harbor

Whether you're an active traveller or just want to take in the scenery, Sag Harbor is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • LongHouse Reserve (5 mi / 8 km)
  • The Hamptons Beaches (5 mi / 8.1 km)
  • Georgica Beach (5.9 mi / 9.6 km)
  • East Hampton Main Beach (6.4 mi / 10.3 km)
  • Sunset Beach (6.5 mi / 10.5 km)
  • Crescent Beach (6.6 mi / 10.5 km)

Transport to and around Sag Harbor

The nearest airport is in East Hampton, NY (HTO), located 3.5 mi (5.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Montauk, NY (MTP), which is 19.8 mi (31.9 km) away.

Frequently asked questions

What is the best area to stay in Sag Harbor when booking a holiday rental?
When considering a holiday rental in Sag Harbor, New York, a popular area to stay is the historic district. This charming neighbourhood offers a delightful blend of quaint streets lined with beautifully preserved 18th and 19th-century homes, giving you a true sense of the town's rich maritime history. Staying here puts you within walking distance of the iconic Sag Harbor Whaling and Historical Museum, which provides fascinating insights into the area's past, as well as the picturesque waterfront, superb for leisurely strolls and enjoying stunning views of the harbour.

Another appealing option is the area around Long Wharf, where you can find a range of properties that cater to different tastes and budgets. This lively spot is not only close to an array of dining options and boutique shops but also offers easy access to the nearby beaches, such as Havens Beach, which is ideal for sunbathing and swimming. The number of available rentals in this area tends to be quite substantial, ensuring a variety of choices for visitors.
How much does it cost to rent a holiday home in Sag Harbor?
Prices for holiday rentals in Sag Harbor 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Sag Harbor to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Sag Harbor holiday house rentals?
You can find great discounts on house rentals in Sag Harbor on Vrbo, 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.
Where are the best areas for renting a beach house in Sag Harbor?
For renting a beach house in Sag Harbor, New York, the area surrounding Long Beach is particularly appealing. This charming beach community offers a selection of waterfront properties that provide stunning views of the bay and easy access to sandy shores. Many rentals in this region feature amenities such as spacious decks for outdoor dining, private gardens, and fully equipped kitchens, making them superb for family gatherings or relaxing getaways.

Additionally, the historic district of Sag Harbor itself is a delightful option, where you can find period homes that have been beautifully restored. These properties often include charming interiors, modern amenities such as air conditioning and Wi-Fi, and outdoor spaces ideal for enjoying the warm summer evenings. Being close to the village centre means you can easily explore local boutiques, art galleries, and renowned restaurants. Find your rental near the beach in Sag Harbor.
Are there any houseboat rentals in Sag Harbor?
In Sag Harbor, there are several houseboat rentals available, providing a great experience on the water. These houseboats are typically moored in picturesque locations near the historic village, allowing guests to enjoy beautiful views of the harbour and easy access to local attractions such as the Sag Harbor Whaling and Historical Museum and the charming shops and restaurants along Main Street. See all houseboats in Sag Harbor.
What is the most popular type of holiday rental accomodation in Sag Harbor?
In Sag Harbor, holiday houses are the most popular type of rental, with around 235 available throughout the charming village. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation, making them great for families or groups looking to enjoy the scenic waterfront and nearby beaches. Additionally, there are about 10 cottages that offer a quaint and cosy atmosphere, ideal for a romantic getaway or a peaceful retreat. Several apartments, houseboats, and condos are also available, providing a variety of options for travellers seeking different experiences in this picturesque area.
Are there any family house rentals in Sag Harbor?
In Sag Harbor, New York, there are a considerable number of family-friendly house rentals available, with around 168 options to choose from. This charming village, known for its maritime history and vibrant arts scene, offers a delightful setting for families. Many properties in the area come equipped with spacious living areas, fully equipped kitchens superb for preparing family meals, and outdoor spaces ideal for children to play.

Visitors can explore nearby attractions such as the picturesque Sag Harbor Marina and the historic Whaling Museum, which provide engaging experiences for all ages. The local beaches, including Havens Beach, are a short drive away, offering opportunities for swimming and sandcastle building. See all family-friendly rentals in Sag Harbor.
Can I rent a holiday home with a pool or hot tub in Sag Harbor?
In Sag Harbor, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 164 options to choose from. This picturesque village in the Hamptons offers a range of charming neighbourhoods, each providing a unique seaside experience. Many of the properties come equipped with private pools, luxurious hot tubs, and spacious outdoor areas superb for entertaining or relaxing in the sun.
Can I find long-stay holiday rentals in Sag Harbor?
A long-stay holiday rental in Sag Harbor 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Sag Harbor?
In Sag Harbor, there are numerous pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties feature modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces, including gardens or patios where pets can roam freely.

The charming waterfront village offers a delightful blend of coastal beauty and rich history, making it an attractive destination for those looking to enjoy both relaxation and activity. Nearby, you can explore the scenic beaches, like Havens Beach, which is known for its calm waters and pet-friendly atmosphere, allowing for enjoyable walks along the shore with your furry companions.
Are there any remote work holiday rentals in Sag Harbor?
In Sag Harbor, there is a wide selection of remote work holiday rentals available, with around 226 properties to choose from. This charming seaside village, known for its picturesque waterfront and historic architecture, offers a conducive environment for remote workers. Many of the rentals come equipped with amenities tailored for productivity, including Wi-Fi, dedicated office spaces, and comfortable desk chairs, ensuring a seamless work experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Sag Harbor holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Sag Harbor 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 on Vrbo 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.
What are popular rental amenities in Sag Harbor?
In Sag Harbor, holiday rentals commonly feature a range of amenities that cater to the needs of travellers. Most properties include well-equipped kitchens, complete with microwaves, dishwashers, and essential cookware, dishware, and utensils, making it easy for guests to prepare their own meals. Stovetops are also standard, allowing for a more home-like cooking experience. These amenities ensure a comfortable stay, whether visitors are looking to enjoy a quiet evening in or host a gathering after a day exploring the charming local shops and waterfront.
When is the best time to visit Sag Harbor for a holiday rental?
The best time to visit Sag Harbor for a holiday rental is during the peak season from June to August, with July being particularly popular. This vibrant period attracts travellers seeking a blend of coastal relaxation and cultural experiences. Visitors can enjoy the delightful summer weather, with temperatures averaging in the low to mid-20s Celsius, superb for outdoor activities like sailing, beach outings, and exploring the charming streets lined with boutiques and eateries.

During the summer months, Sag Harbor buzzes with life, offering a number of events, including art shows and music festivals that showcase local talent. The picturesque waterfront and scenic parks provide ample opportunities for leisurely strolls and picnics, making it an ideal time for families and friends to gather.

For those looking for a more budget-friendly option, consider planning your visit in November. While the summer crowds have thinned, this month offers a serene atmosphere, allowing for peaceful walks along the bay and the chance to enjoy the natural beauty of the changing seasons. The crisp autumn air contributes to a unique charm, making it a wonderful time for reflection and relaxation.
How early should I book a Sag Harbor holiday rental?
Book your Sag Harbor holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Sag Harbor?
In Sag Harbor, visitors can enjoy a blend of historical charm and coastal beauty. The Sag Harbor Whaling & Historical Museum offers insights into the town's rich maritime history and is a must-visit for history enthusiasts. The picturesque Main Street, lined with boutiques and eateries, provides a lovely setting for leisurely strolls and dining experiences.
Can I change or cancel my Sag Harbor home rental booking on Vrbo?
To find Sag Harbor holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Sag Harbor holiday rental prices shown on Vrbo?
Vrbo 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.

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