Vacation rentals in Northwest Woods

A charming cottage is illuminated warmly at night, showcasing a welcoming entrance. A well-lit pathway lined with soft ground lights leads toward the front door, framed by the surrounding wooded area. The exterior features a classic design, with wooden siding and inviting windows.

4.95 out of 5 average rating, 233 reviews

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

4.95 out of 5 average rating, 435 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

A serene outdoor area features a heated saltwater pool surrounded by a brick patio. Lounge chairs with colorful cushions are arranged beside the pool, and a blue umbrella provides shade nearby. Lush greenery borders the space, enhancing the tranquility of the environment.

4.86 out of 5 average rating, 207 reviews

HeatedSaltWaterPool, Walk2PrivateBeach, Yard4Dog

Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community.Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset. Easy living home.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

Guest suite in East Hampton

A serene beach scene features soft, golden sand curving along the shore, meeting gentle waves that lap at the water's edge. The horizon showcases a calm, blue ocean under a sky filled with wispy clouds, creating a tranquil atmosphere.

4.79 out of 5 average rating, 189 reviews

Serenity Near the Beach

Perfectly situated near beaches, waterfront dining , town, and art sites. Peaceful private room and full bathroom with private entrance from outside. Equipped with everything you need to enjoy beach. Enjoy beautiful view of natural setting from deck. We provide microwave, coffee maker, mini refrigerator, dishware, and table in room and outdoors - does not include living room or kitchen. Perfect for work or vacation. Space attached to the house but 100% private. No smoking. No children.

A large swimming pool is surrounded by a spacious wooden deck featuring sun loungers and umbrellas for shade. The modern home is visible in the background, highlighted by expansive glass doors and a serene garden setting.

4.93 out of 5 average rating, 154 reviews

Large heated pool, games room, near private beach

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (opens 04/25 and closes mid-October (there's an additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool or take a 15 min walk to private bay beach to swim and paddle board. Or drive 15mins to the Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg RR-25-399 Local taxes included

4.98 out of 5 average rating, 176 reviews

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.

Apartment in Sag Harbor

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!

Guesthouse in East Hampton

The kitchenette features a small refrigerator, microwave, countertop oven, and a Keurig coffee maker. A rack displays various coffee pods, and a paper towel holder is positioned nearby. Light-colored cabinetry provides ample storage space above the countertop.

4.82 out of 5 average rating, 319 reviews

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house with use of amenities (shared with our family of 4). The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, micrwave, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for guests. 2 Adult guests ONLY (no children) due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets.

The image displays a tranquil swimming pool illuminated in soft turquoise light at night. Adjacent to it, a hot tub is visible, sending gentle bubbles to the surface. Surrounding greenery is faintly visible, contributing to a serene outdoor atmosphere.

4.84 out of 5 average rating, 100 reviews

East Hampton Oasis - Pool and Hot Tub

Nestled at the end of a private road in the Springs section of East Hampton, this classic Hamptons home will keep you and your friends/family entertained. Living room with sonos sound system, kitchen, 3 bedrooms, 2 bathrooms, outdoor living area with lounge chairs, a bbq, bar, pool and hot tub. All 3 bedrooms have AC. Towels and linens provided. Washer/dryer available. CLOSE TO BEACH AND EH VILLAGE. The pool is open May 5 through September 24. The hot tub remains open year round.

Guest suite in East Hampton

A clear, inviting pool is framed by a spacious patio area. Four blue lounge chairs with vibrant green and white cushions are positioned alongside the pool, providing a relaxing space to enjoy the outdoors. Lush greenery and colorful flower pots enhance the surrounding ambiance.

4.96 out of 5 average rating, 165 reviews

B our guest! Central 2 all Prvt entrance Prvt Pool

Beautiful, bright, spacious King suite w fireplace, two bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book/movie! The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w your choice of pillows. Complimentary coffee/tea/snacks and breakfast treats provided.

4.94 out of 5 average rating, 187 reviews

Home in Greenport

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

5 out of 5 average rating, 13 reviews

A wrap-around balcony provides sweeping views of Gardiner’s Bay. Comfortable lounge chairs are positioned for relaxation, while the clear sky reflects over the water. The area offers a serene setting for enjoying the outdoors.

Home in East Marion

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

Guest suite in Sag Harbor

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.

4.9 out of 5 average rating, 356 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. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

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Other great vacation rentals in Northwest Woods

A bright living area features a spacious cream-colored sofa, inviting natural light through multiple large windows and French doors. The wooden dining table and colorful chairs are visible in the background, overlooking a serene view of the outdoor landscape.

5 out of 5 average rating, 16 reviews

Renovated 4Bedroom Farmhouse Pool Steps from Beach

SarahRating, 5 stars8 months ago

We had such a lovely time at Morgan’s home! She was extremely responsive and even allowed us to check in early as well as leaving baby items for us to use. Our dog loved the fenced in yard and despite the rain ruining our pool plans, we had a cozy wonderful stay. We had an absolutely lovely stay and can’t wait to return next summer!

Guesthouse in East Hampton

A gunnite pool is surrounded by a well-maintained lawn and natural greenery. Sun loungers are positioned along one side, while two chairs invite relaxation beneath the shade of nearby trees. Bright blue skies and fluffy white clouds reflect in the clear pool water.

4.9 out of 5 average rating, 211 reviews

Beautiful Airy Barn in Springs

NadineRating, 5 stars6 days ago

10000/10 recommend. Amazing Airbnb, beautiful pool, near east Hampton, Montauk, Parrish art museum, Dan Flavin institute, longhouse reserve, pollock krasner house. Easy check in, VERY safe neighborhood, Gilliam and her husband were kind and helpful.

A wooden deck features comfortable seating with white cushions, positioned around a small table set with tea and pastries. Lush green grass surrounds the area, dotted with tall trees, while a clear view of the harbor can be seen in the background.

4.82 out of 5 average rating, 28 reviews

Historic East Hampton Home - Private Beach Access

KyleRating, 5 stars1 month ago

Elizabeth was a wonderful host - we traveled with a toddler and an infant and Elizabeth could not have been more accommodating. She was so responsive and friendly before and during the entire trip. The house and property are absolutely beautiful— you can’t beat being able to walk right down to the beach. Highly recommend!

A serene coastal landscape is depicted, featuring a sandy beach bordered by tall grasses. Gentle waves lap at the shore under a sky painted with soft pastel colors. The distant horizon meets the water, while a cluster of bushes adds texture to the scene.

4.97 out of 5 average rating, 72 reviews

Cedar Cottage

FrankRating, 5 stars9 months ago

Wonderful! We were looking for an end of summer getaway to relax and de-stress; the Cedar Cottage of East Hampton was a perfect fit. Very comfortable, well equipped kitchen, fun outdoor deck, great beach, easy access to Sag Harbor or East Hampton. Thanks for all!

A spacious dining area features a large wooden table surrounded by crafted chairs. Natural light floods the room through tall, Art Deco windows, illuminating the clean white walls and polished wooden flooring. The fireplace adds warmth, complementing the open layout with a view of the staircase.

4.6 out of 5 average rating, 15 reviews

4 Min Walk to the Beach!

LizetRating, 5 stars11 months ago

Beautiful Beautiful Amazing memories created Thank you so much!

4.9 out of 5 average rating, 20 reviews

East Hampton Secluded Escape with Gunite Pool

MartaRating, 5 stars2 weeks ago

The place was clean, spacious and cozy. Allen was quick to respond to our messages and concerns. Thank you for being a great host.

A modern kitchen features sleek cabinetry and dark granite countertops. A farmhouse sink is positioned beneath a window overlooking the outdoors. An open layout allows for a clear view into the adjacent dining area, where natural light illuminates the space.

4.81 out of 5 average rating, 16 reviews

Luxurious East Hampton Retreat

JeromeRating, 5 stars10 months ago

We had a great week in this beautiful home. It was spacious, clean and private which was exactly what we were looking for. It has a really nice pool too that gave us a much needed break from the sun on the beach. We will try to book this house again next year and highly reccomend it to others as well.