Sag Harbor holiday lettings

We found 2,557 holiday rentals — enter your dates for availability

Discover a selection of 307 homes, 12 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:5 Jun - 12 Jun

Image gallery for Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

Private pool
9.8 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

Southampton

12% off
Price is £11,711
for 7 nights, 1 home
£1,673 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

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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)
  • 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)
  • Pindar Vineyards (9.3 mi / 14.9 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)
  • East Hampton Village Nature Trail and Wildlife Sanctuary (6.4 mi / 10.3 km)
  • Sunset Beach (6.5 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, a charming village with a rich maritime history, the area around the waterfront is particularly appealing. This neighbourhood offers a delightful mix of quaint shops, art galleries, and excellent dining options, all within easy reach of the picturesque harbour. One of the top attractions nearby is the Sag Harbor Whaling Museum, where visitors can delve into the town's whaling past and maritime culture. Additionally, the beautiful beaches, such as Havens Beach, provide a great spot for relaxation and enjoying the stunning views of the bay.

For those looking to immerse themselves in the local scene, the area around Main Street is vibrant and lively, featuring a variety of properties that cater to different tastes and budgets. The charming architecture and historic buildings add to the area's allure, making it a picturesque place to stay.
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, consider the picturesque waterfront areas near the village centre, where charming properties often boast stunning views of the harbour and easy access to local beaches. The area around Havens Beach is particularly appealing, with several holiday rentals featuring amenities such as outdoor patios, swimming pools, and private docks, superb for families or groups wanting to enjoy a quintessential beachside experience.

Additionally, the North Haven section offers a more tranquil atmosphere, with upscale homes that typically come equipped with modern kitchens, spacious living areas, and easy access to secluded beaches. Many of these properties also include outdoor entertainment spaces, ideal for summer barbecues or relaxing evenings by the water.

For those interested in local culture, Sag Harbor's vibrant village offers a variety of shops, art galleries, and restaurants, making it an excellent base for exploring the area. Rentals close to the main street often provide convenient access to these amenities while still maintaining proximity to the beach, giving travellers the best of both worlds. 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 unique way to experience this charming coastal village. These houseboats often feature modern amenities such as fully equipped kitchens, spacious decks for sunbathing or dining al fresco, and comfortable living areas superb for relaxing after a day of exploring. The rentals are typically moored in scenic locations, allowing guests to enjoy views of the harbour and easy access to local attractions like the historic Whaling Museum and the picturesque Sag Harbour Marina.
What is the most popular type of holiday rental accomodation in Sag Harbor?
In Sag Harbor, holiday houses are the most popular type of holiday rental, with around 768 available throughout the charming town. These properties offer a spacious environment, typically featuring multiple bedrooms, fully equipped kitchens, and outdoor areas like decks or gardens, great for enjoying the coastal atmosphere. The holiday houses are often situated close to local attractions such as the picturesque harbour, shops, and restaurants, enhancing the overall experience for travellers.

Additionally, there are about 36 apartments and 32 cottages available, which provide a more compact yet comfortable option for couples or smaller groups. These rentals generally include essential amenities such as kitchen facilities and cosy living spaces. Though fewer in number, houseboats and condos also contribute to the diverse rental offerings in Sag Harbor, suiting those seeking great experiences on the water or in more communal living settings.
Are there any family house rentals in Sag Harbor?
In Sag Harbor, there are plenty of family-friendly house rentals available, with around 131 properties to choose from. This charming village is situated near the beautiful beaches of the Hamptons, making it an ideal spot for a family getaway. Many of these homes boast spacious living areas, fully equipped kitchens, and outdoor spaces superb for barbecues or simply enjoying the fresh air.

Visitors can find properties with amenities such as private pools, game rooms to keep the children entertained, and comfortable bedrooms for restful nights. The neighbourhood is also close to local attractions like the picturesque Sag Harbor Village, where families can explore quaint shops and enjoy waterfront dining. Moreover, nearby beaches provide opportunities for swimming, sunbathing, and beach games, ensuring a delightful experience for guests of all ages.
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 or hot tubs, with approximately 126 options to choose from. This picturesque village, located on the eastern end of Long Island, is known for its charming waterfront and vibrant arts scene. Properties with these amenities can be found in various neighbourhoods, including the serene residential areas surrounding the bay and the more bustling parts near the village centre.

Travellers can expect a range of amenities in these rentals, such as private swimming pools, inviting hot tubs, spacious outdoor decks, and fully equipped kitchens ideal for family gatherings or entertaining guests.
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 variety of options for travellers with pets. Many of these homes are equipped with modern amenities such as well-appointed kitchens, spacious living areas, and outdoor spaces where pets can roam freely.

The charming village atmosphere of Sag Harbor is complemented by its proximity to beautiful parks and waterfront areas. Nearby, places like the Sag Harbor Village Marina offer scenic walks along the waterfront, making it a lovely spot for pet owners to enjoy time outdoors with their furry companions.

Additionally, the area features pet-friendly beaches, allowing for enjoyable days by the sea with pets. Rentals here can vary from quaint cottages to more luxurious homes, often featuring private gardens or patios, great for relaxing after a day of exploring.
Are there any remote work holiday rentals in Sag Harbor?
In Sag Harbor, New York, there are numerous holiday rentals suitable for remote work, with around 756 options available. This charming village, known for its maritime history and vibrant arts scene, offers a variety of properties that cater to the needs of remote workers. Many rentals come equipped with reliable Wi-Fi, ensuring seamless connectivity for video calls and online tasks.

Travellers can expect a range of amenities, including dedicated workspaces, comfortable furnishings, and spacious living areas that provide a conducive environment for productivity. Some properties also feature outdoor spaces, great for taking breaks and enjoying the scenic views of the surrounding area.

The village itself is home to lovely shops, restaurants, and galleries, creating an inspiring atmosphere for those working remotely. 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, popular rental amenities include fully equipped kitchens, allowing travellers to prepare meals at their convenience. Many properties also feature outdoor decks or patios, superb for enjoying the tranquil surroundings. A fireplace is a common addition, providing a cosy atmosphere during cooler evenings. Additionally, amenities such as blenders are available for those who enjoy smoothies or homemade drinks. Onsite parking is another practical feature that many rentals offer, ensuring easy access for guests arriving by car.
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 summer months, particularly in July, when the town comes alive with vibrant energy and a variety of activities. This peak season, spanning from June to August, attracts many visitors eager to enjoy the scenic beauty of the Hamptons, with its picturesque beaches and charming village atmosphere.

In July, you can expect warm temperatures averaging around 25 to 30 degrees Celsius, superb for outdoor pursuits like swimming, sailing, or exploring the local boutiques and art galleries. The lively summer events, including farmers' markets and art fairs, add to the allure, making it an ideal time for those looking to immerse themselves in the local culture.

For those seeking a more tranquil experience, consider visiting in November. This month offers a serene atmosphere, allowing you to appreciate Sag Harbor's historic charm without the summer crowds. The fall foliage adds a beautiful backdrop for leisurely walks along the waterfront or cozy evenings in a holiday rental.

Ultimately, your choice of when to visit Sag Harbor will depend on whether you prefer the bustling vibe of the summer or the peaceful charm of the off-peak months.
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 engage in a charming coastal atmosphere with a rich maritime history. The Sag Harbor Whaling and Historical Museum offers insights into the town's whaling past and features intriguing exhibits in a beautifully preserved building. The picturesque waterfront area is superb for leisurely strolls, and you can find lovely views of the harbour from various spots along Main Street.

For those interested in art and culture, the Bay Street Theatre hosts a variety of performances and events throughout the year, making it a cultural hub in the area. Nearby, the scenic Long Beach provides a great spot for sunbathing and enjoying the summer breeze.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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