Holiday rentals in Sag Harbor

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Top-rated holiday rentals in Sag Harbor

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
A serene backyard features a landscaped area surrounding a salt-water pool. Sun loungers line the pool's edge, with vibrant greenery and flower beds enhancing the peaceful setting. A grassy area is visible beyond the pool, providing additional outdoor space.
Guest suite in Sag Harbor
4.88 out of 5 average rating, 8 reviews

Sag Harbor PrIvate Entry Guest Suite + Pool

Separate Private Guest suite/APT. 1 king bed in the Bedroom w bathroom and 1 queen in the common area. Best for close relationships to rent because the bathroom is IN the bedroom Salt Water Pool. location 5 min to Sag harbor Bridgehampton. 8 min to the Ocean. Walkable? to Bay Beach/ Sag Village both about 1.5 miles. Crisp and clean with your own bedroom and bath, plus kitchenette washer & dryer. The Apt is in the private Lower Level walkout in the home In Summer SHARED POOL Open MD to Sept 20th

Superhost
Guest house in Sag Harbor
4.86 out of 5 average rating, 115 reviews

Charming 2BR Cottage, Walk to Town

Beech Tree Cottage is a charming 2-bedroom, 1-bath, two-story cottage conveniently located in the peaceful historic district of Sag Harbor, NY. It is a 5-minute walk along the waterfront to Main Street and the center of the village. PLEASE NOTE: We are currently only accepting week- or month-long stays for July and August. We will open up forshort stays in summer subject to availability after May 15. (Short stays are ok in other months.) Please review our house rules before making an inquiry.

Guest favourite
A charming two-story house features a light exterior with contrasting blue shutters. A white picket fence with hydrangea plants encloses the front yard, while trees provide shade. The sloped roof adds character, and the surrounding greenery enhances the home's inviting presence.
Home in Sag Harbor
4.9 out of 5 average rating, 113 reviews

Walk to Village Sag Harbor Victorian

Charming 2 bedroom 2 bathroom house in the historic Village of Sag Harbor with view of pond and park. Walking distance (not driving) to the quaint village with restaurants, shops, long wharf, gym, yoga. Living room with fireplace, dining room, kitchen and office. Upstairs loft ensuite bedroom and bathroom. Downstairs bedroom and full bath with tub and shower. Flower filled back deck with BBQ. Wireless internet, 2 TV's, air conditioner units, washer dryer. Minutes to ocean and bay beaches.

Guest favourite
Home in Hampton Bays
4.85 out of 5 average rating, 146 reviews

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Top guest favourite
A charming orange house with white shutters features a welcoming front entry. Four large windows, adorned with flower boxes, enhance the inviting appearance. Lush greenery surrounds the front yard, complemented by neatly trimmed bushes and a pathway leading to the entrance.
Flat in Sag Harbor
4.99 out of 5 average rating, 222 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Guest favourite
The exterior of a spacious two-story house is highlighted, surrounded by lush greenery. A clear saltwater pool features a light blue hue, with several lounge chairs positioned along the patio. Large windows adorn the house, inviting natural light into the interior.
Home in Sag Harbor
5 out of 5 average rating, 7 reviews

Designer home in Sag Harbor : 5BR walk to beach

Nestled in Sag Harbor, this elegant 5-bedroom home offers a saltwater heated pool just 2 miles away from the town. A mere five-minute stroll takes you to the Serene Green local farm stand and Long Beach Bay, where you can indulge in swimming, paddleboarding, and witnessing breathtaking sunsets. The chef's kitchen is perfect for culinary adventures, and you can savor your meals either poolside under the charming string lights at the 8-person farm table or indoors at the 8-person table

Top guest favourite
An inviting outdoor sitting area features wooden chairs positioned near French doors. The space is surrounded by lush greenery, and a stone pathway leads to the entrance of the studio apartment. Flowering vines and potted plants add a touch of nature.
Guest suite in Sag Harbor
4.9 out of 5 average rating, 397 reviews

Artists Sag Harbor Village Retreat

This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Fully self contained and private. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking in driveway close to entrance. Not suitable for infants or children.

Top guest favourite
Flat in Sag Harbor
4.94 out of 5 average rating, 142 reviews

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

Guest favourite
A bright and airy living space features a comfortable white sofa adorned with purple accents. Natural light pours in through large windows, illuminating the open-plan kitchen with modern appliances. A cozy wood stove complements the warm wood flooring, inviting relaxation in the room.
Cottage in Sag Harbor
4.97 out of 5 average rating, 88 reviews

Charming Scandinavian Inspired Beach Cottage

Steps from Circle Beach. Charming 2 bed/ 2.5 bath w a separate studio w a twin daybed and 1/2 bath, outdoor shower, large outdoor entertaining patio with a grill. The master bed has a queen bed and the bunk room has a full bed w a twin on bed on top. Located in the cute beach community of Pine Neck, this is Sag Harbor's best kept secret! Chef's kitchen is equipped with top of the line appliances and gadgets. The master bathroom features a clawfoot soaking tub.

Top guest favourite
Home in Sag Harbor
4.89 out of 5 average rating, 111 reviews

The Cooper-Burke House

Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

Guest favourite
Home in Sag Harbor
4.95 out of 5 average rating, 317 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

Guest favourite
Home in Sag Harbor
4.86 out of 5 average rating, 167 reviews

Sag Harbor House for rent.

3 bedroom 2 bath Cape Cod less than 1 mile to the great village of Sag Harbor. Brand new kitchen. Beautiful beaches are just a short drive or jog away. Perfect getaway spot where you can walk or cycle to town or beach. BBQ out back or walk into town for a bite.

Popular amenities for Sag Harbor holiday rentals

When is the best time to visit Sag Harbor?

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Avg. price€444€364€351€390€561€648€765€843€607€433€459€472
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Frequently Asked Questions

  • What are the best places to stay in Sag Harbor?

    Sag Harbor has inviting accommodations in its historic village center, near the marina, and around wooded neighborhoods. Many vacation rentals blend traditional and modern styles, creating a comfortable base for exploring the area’s shops, local dining, and nearby beaches.

  • What are the best things to do in Sag Harbor with kids?

    Families frequently suggest visiting local parks, exploring the marina, or joining a boat tour. The Whaling Museum has interactive exhibits, and nearby beaches provide space for sandcastle building and relaxation.

  • What are some of the best things to do in Sag Harbor?

    Explore the Sag Harbor Whaling Museum, stroll along the marina, or discover local art galleries. Visitors often enjoy boat tours, browsing boutiques, and dining at waterfront restaurants with locally rooted flavors.

  • How is the weather in Sag Harbor?

    Sag Harbor has chilly winters around 25–44°F (-4–7°C) and warm, pleasant summers near 66–83°F (19–28°C). Expect higher rainfall in spring and late autumn, with drier, breezier conditions during summer months.

  • When is the best time to visit Sag Harbor?

    Late spring through early fall is often recommended for Sag Harbor, when temperatures are mild and outdoor activities are popular. Festivals and community events frequently take place during these seasons.

  • What are the best places to visit in Sag Harbor?

    Frequently suggested stops include the Sag Harbor Whaling Museum, Long Wharf, and local art galleries. Strolling through the historic village and relaxing at nearby beaches can give you a sense of the area’s charm and maritime heritage.

  • What are some hiking trails in Sag Harbor?

    Sag Harbor has nature preserves and wooded paths where visitors can enjoy gentle hiking, birdwatching, and seasonal foliage. The area’s trails are often lined with oak and pine, providing a peaceful escape near the village.

  • What are some family activities we can do in Sag Harbor?

    Families can explore hands-on exhibits at the Sag Harbor Whaling Museum, relax at nearby beaches, or rent kayaks for harbor paddling. Parks and open spaces around the village also welcome picnics and casual play.

  • What are some of the best day trip ideas from Sag Harbor?

    Explore historic villages on the East End, visit local vineyards, or discover nature preserves around the peninsula. Coastal hamlets and art-filled towns nearby have galleries, farm stands, and maritime history displays.

  • Are there any pet friendly accommodations available in Sag Harbor?

    Sag Harbor has pet-friendly vacation rentals in the village and surrounding residential areas. Some accommodations may welcome dogs, making it easier for travelers to bring their companions along for coastal walks.

  • What are some local tips for visiting Sag Harbor?

    Explore on foot to enjoy the village’s streets, and look for local art installations and independent shops. Early mornings around the harbor are quieter, and farmers’ markets frequently showcase regional produce and baked goods.

  • What is Sag Harbor known for?

    Sag Harbor is known for its maritime history, historic village character, and vibrant arts scene. The community has a legacy of shipbuilding and whaling, reflected in local museums and waterfront architecture.

  • What are the best hidden gems to explore in Sag Harbor?

    Visitors often suggest checking out independent bookstores, small art studios, and tucked-away bakeries in Sag Harbor. Less-traveled trails in local preserves invite quiet moments among trees and native plants.

  • What are the best foods to try in Sag Harbor?

    Local menus frequently feature fresh seafood like clams and oysters, as well as seasonal produce from East End farms. Bakery treats, small-batch ice cream, and classic lobster rolls are also popular with visitors and locals.

  • What should I bring for a trip to Sag Harbor?

    Pack layers for shifting weather, comfortable footwear for village walks, and a light jacket for breezy evenings near the water. A reusable water bottle and sun protection are helpful during outdoor excursions.

  • What is the nightlife in Sag Harbor like?

    Sag Harbor’s nightlife has a relaxed atmosphere with wine bars, local restaurants, and occasional live music at small venues. Evening strolls along the marina and casual gatherings are a hallmark of the area.

  • What are the most popular events or festivals in Sag Harbor?

    Sag Harbor has arts festivals, boating celebrations, and outdoor performances, frequently suggested during late spring through early fall. Community fairs and seasonal markets are often highlights for visitors and locals.

  • Are there family friendly vacation rentals in Sag Harbor?

    The Sag Harbor area has family-friendly vacation rentals with amenities like full kitchens, backyard spaces, and proximity to parks or beaches. Many homes are designed for groups of various sizes, creating an inviting atmosphere for travelers with children.

Quick stats about holiday rentals in Sag Harbor

  • Total holiday rentals

    Explore 260 holiday rentals in Sag Harbor

  • Nightly prices starting at

    Sag Harbor holiday rentals start at €78 per night before taxes and fees

  • Verified guest reviews

    Over 7,440 verified reviews to help you choose

  • Family-friendly holiday rentals

    200 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 110 rentals that welcome pets

  • Holiday rentals with a pool

    120 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wifi availability

    260 of Sag Harbor holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Beachfront, Gym and BBQ grill across Sag Harbor rentals

  • 4.9 Average rating

    Sag Harbor stays are highly rated by guests – averaging 4.9 out of 5!

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