Fitness-friendly vacation rentals in Cutchogue

4.86 out of 5 average rating, 28 reviews

The exterior of the beach bungalow is illuminated at dusk, showcasing large windows that reflect warm light. Surrounded by mature trees, the spacious lawn contrasts with the building's neutral tones, creating a serene atmosphere. The driveway hints at the inviting interior.

Bungalow in The Hamptons

Civilian Surf Club: a family-friendly beach house

Iconic 70’s beach bungalow & pool nestled in a private 3/4 acre plot surrounded by mature oaks and evergreens. Our home is intentionally appointed by interior designers, filled with collectibles, art & antiques. Embrace the ‘Hamptons Bohemia’ feel, with a vaulted living room, ample seating, a wood burning fireplace and an outdoor area with a sprawling cedar deck & a heated pool. Located within walking distance of the bay beaches and an 8 min drive to Ponquogue beach & The Bowl Spot for surfing.

4.88 out of 5 average rating, 234 reviews

A living area features a gray futon adorned with decorative pillows, complemented by a small coffee table. A red accent chair provides additional seating. Soft lighting from the ceiling enhances the space, while wall art depicts blooming flowers, contributing to a welcoming atmosphere.

Apartment in Patchogue

Private 1br Apartment on Long Island

Bright & clean 1br apartment with private entrance on a quiet street. Refrigerator, microwave, keurig incl 2 miles to downtown restaurants, bars, breweries, shopping 10 miles to winery & vineyards 3 miles to beaches 3 miles to Fire Island Ferry 30miles to NYC 3 miles to Baseball Heaven 10 miles to Stonybrook University & hospital 1 mile to public horse farm & stable 3 miles to St Joseph's College .5 mile to Long Island Community Hospital 1 mile to hiking 45min to JFK 10min to McArthur airport

An open-concept living space features a dining area with a rectangular wooden table adorned with a decorative bowl. A spacious couch is positioned near a fireplace, with large windows allowing ample natural light. A stylish chandelier hangs above, complementing the high, pitched ceiling.

4.99 out of 5 average rating, 108 reviews

East Hampton Village Fringe, Renovated with Pool

This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

4.99 out of 5 average rating, 138 reviews

A comfortable living room is featured, with a gray sofa and two wooden chairs positioned around a small, circular coffee table. Natural light filters through large windows, illuminating light-colored walls and warm wooden flooring.

Home in Milford

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

4.85 out of 5 average rating, 41 reviews

An open living area features high ceilings and large windows that bring in natural light. A sectional sofa in deep blue surrounds a vibrant orange rug, while an artwork adorns the wall. A dining area with a wooden table and chairs can be seen in the background.

Home in Riverhead

North Fork True Beachfront Home

This is New York version of California's Big Sur, with direct beach access and spectacular water views, surrounded by forest. Modern, 3,000 sq feet. Walk down path from house to a fantastic sand beach with lifeguard. Large deck for lounging, BBQ, and sunset views. 4 bedrooms, 3 baths, outdoor shower, 4 person hot tub, 2 person sauna, separate den w/home theater, gym, hammocks, wood burning fireplace. Experience the Long Island Sound without neighbors and the suburbs; a naturalist's haven.

A spacious outdoor area features a heated gunite pool surrounded by sun loungers and greenery. The villa is visible in the background, showcasing large windows and a blend of natural materials. Shade is provided by overhanging trees scattered around the property.

4.98 out of 5 average rating, 47 reviews

Incredible 9+ Bed Watermill Home Wellness Retreat

Luxury 9000 SF Southampton villa with a heated gunite pool, hot tub, steam shower & sauna, 9-bedroom, 8.5-bathroom, nestled on a quiet cul-de-sac in Watermill. Bright with large windows, e-shades in bedrooms, indoor/outdoor sound system, W/D on every floor (3 sets). Formal dining/living area, chefs' kitchen, TV room, movie room, gym, outdoor kitchen, arcade, pool table, air hockey and foosball. Please read our disclosures & house manual. Not a party house and no events permitted.

A lush backyard features a children's playset alongside a hammock. Adirondack chairs are arranged around a fire-pit, framed by trees and greenery. A serene waterfront view is visible, with a dock extending into the calm waters, enhancing the natural landscape.

5 out of 5 average rating, 104 reviews

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

4.96 out of 5 average rating, 104 reviews

A spacious farmhouse is showcased, featuring a welcoming porch with an American flag. The exterior is adorned with dark wooden shingles and large windows. Lush green lawn and well-maintained flower beds enhance the inviting curb appeal under a clear blue sky.

Home in North Fork

Stunning Farmhouse in NoFo I Heated Pool, Wineries

Chic & Luxurious North Fork Farmhouse Retreat Set on a private 1-acre lot, this stylish farmhouse offers a pool, lounge areas, and refreshing ocean breezes. Just 1.5 hours from NYC, you’ll be minutes from beaches, wineries, farm stands, hiking, and golf. Inside, enjoy modern interiors, a full kitchen, and fast Wi-Fi. Perfect for families, couples, or friends, this retreat is ideal for a peaceful escape, remote work, or exploring wine country near the Hamptons and North Fork.

A spacious living area is illuminated by natural light from large windows. A comfortable sofa and armchair are arranged around a low coffee table. A dining table with six chairs sits adjacent, while the kitchen is visible in the background. A staircase leads to the upper floor.

4.94 out of 5 average rating, 143 reviews

Modern 5BR Getaway • Close to Beaches & Wineries

⭐ Rated 4.95 with 135+ glowing reviews! This modern 5BR, 4BA Hampton Bays retreat sleeps 10 and is just minutes from beaches, dining, and shops. Enjoy open living spaces, Smart TVs, and fast WiFi. The finished basement features ping pong, a gym, and lounge, while the backyard offers a BBQ, patio, and outdoor seating. Beach gear is included, making it easy to explore. Perfect for families or groups seeking the ultimate Hamptons getaway with comfort and style.

A well-designed outdoor area features a pristine pool with colorful floats, bordered by a spacious deck. Lounge chairs, adorned in striped blue and white, provide comfortable seating under large umbrellas. The house is illuminated, showcasing a welcoming atmosphere amidst lush greenery.

4.98 out of 5 average rating, 66 reviews

Insta: @staywithhamptonsmama PINKWOOD PLAYHOUSE is the perfect spot for your Hamptons stay, offering elevated design and relaxed luxury with laid back beach vibes. Perfect for families or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings and an open floorplan. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool.

A spacious outdoor area features a large swimming pool surrounded by lush green grass. Four lounge chairs are positioned nearby, alongside a parasol offering shade. A quaint shed with red accents is visible in the background, complemented by seating areas. Tall trees provide a natural backdrop.

5 out of 5 average rating, 16 reviews

Sag Harbor Dream Home: Heated Pool

Just minutes from Main Sreet in Sag Harbor, Long Beach, Wolffer Vineyard, and Sagg Main Beach, this home is a perfectly located, brand-new gut remodel, with over 3500sqft interior and an entertainer's dream yard - on a quiet cul-de-sac street. A stylish experience at this centrally-located escape! Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

An open-concept living space features a circular marble dining table surrounded by light wooden chairs. A spacious kitchen with modern cabinetry is visible, alongside large glass doors that provide unobstructed views of the harbor and bay. Natural light fills the room through the skylight.

5 out of 5 average rating, 25 reviews

Designer East Hampton with Bay Views + Pool

Direct Harbor & Bay Views- Designer renovated 4 bedroom/3.5 bath East Hampton pool home has the wow factor! Nestled on a half acre in prime East Hampton, the home sits on the highest lot in the neighborhood allowing incredible views of Three Mile Harbor and Gardiners Bay. A short 5 minute drive to Main Street and 8 minutes to East Hampton Beach! Please note: Pool is open from June 1- September 15

Popular amenities for Cutchogue fitness-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

A serene view of the harbor is captured, showcasing gentle waves and sailboats anchored in the water. Lush green grass and tall trees frame the scene, providing a tranquil backdrop to the picturesque waterfront. The expansive sky is clear, allowing ample sunlight to illuminate the landscape.

Apartment in Shelter Island Heights

5 out of 5 average rating, 7 reviews

CHIC WATER VIEW APT. ON SHELTER ISLAND

Superhost

A modern living area is showcased, featuring a plush blue sofa and a cozy cream armchair. A flat-screen TV is positioned on a light wooden media console. Decorative art pieces adorn the walls, with natural light filtering through the window.

Apartment in Milford

4.65 out of 5 average rating, 20 reviews

Downtown Milford New,Train Access,Pets,Gym,Unit E3

An inviting living area showcases a spacious layout with plush seating and natural lighting. A wooden dining table, surrounded by chairs, offers a comfortable space for meals. A staircase leads to an upper level, and a rocking chair is positioned nearby, enhancing the cozy ambiance.

Apartment in Mount Sinai

4 out of 5 average rating, 3 reviews

Lovely 1-bedroom basement apartment in Mt. Sinai

4.93 out of 5 average rating, 15 reviews

An open-plan studio is featured, with a plush green sofa adorned by decorative pillows. A spacious bed is positioned in the background, surrounded by framed art. Light-colored cabinetry and modern appliances comprise the kitchenette area, while a coffee table and decorative items enhance the inviting space.

Apartment in Milford

Downtown Milford New,Train Access,Gym,Unit 2A

A bright living space features a spacious bed with light bedding, flanked by bedside lamps. A dining table with four chairs is set nearby, accompanied by a decorative centerpiece. Natural light fills the area, enhancing the neutral color palette and inviting ambiance.

Private room in The Hamptons

Luxurious Open Floor Plan - Walk to Village

A serene outdoor space features a rectangular swimming pool surrounded by decorative stone pavement. Two statues stand at the pool's edge, while a swing chair is positioned nearby. Lush greenery is present, and a multi-story white house is visible in the background near the pool.

Private room in Setauket- East Setauket

4.88 out of 5 average rating, 16 reviews

Private room 5 minutes from Stony Brook University

5 out of 5 average rating, 9 reviews

A serene view of the water is captured under a cloudy sky, with sunlight reflecting off the surface. The horizon features a gentle gradient of blues and silvers, offering a calming atmosphere. Soft waves can be seen in the foreground, enhancing the tranquil scene.

Apartment in Milford

Walk to the beach

Fitness-friendly house rentals

5 out of 5 average rating, 31 reviews

A stylish living area showcases a comfortable sofa and accent chairs arranged around a modern coffee table. Warm wood flooring complements the dark walls, and soft lighting is provided by a chandelier. Large windows are dressed with elegant drapes, inviting natural light into the space.

Home in North Fork

Elegant Greenport Victorian -Winter Harbor House-

4.93 out of 5 average rating, 45 reviews

A bright living room features two blue sofas facing a circular coffee table. A bookshelf holds decorative items and a guitar leans against the wall. Large windows with grey curtains allow natural light to illuminate the space, creating a cozy atmosphere.

Home in Milford

3br/2ba: Quiet & Cozy Getaway in Milford

An outdoor space featuring a saltwater pool with a jacuzzi positioned nearby. A patio area includes an umbrella and ample seating options. Lush green grass surrounds the pool, while two white decorative swan floats are visible on the water, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 49 reviews

Hamptons Vacation Rental w/ Heated Pool & Jacuzzi!

A spacious heated in-ground pool is surrounded by a stone patio and vibrant landscaping. Lounge chairs are arranged along the poolside, accompanied by a large umbrella for shade. Lush greenery and blooming flowers frame the area, creating a serene outdoor retreat.

4.97 out of 5 average rating, 72 reviews

4 BR Hamptons Oasis w/ Pool,Jacuzzi & Beach Access

A modern kitchen equipped with wooden cabinetry features a central island topped with dark stone. The space is illuminated by pendant lights, while glass doors offer views of the pool outside. Wall decor includes woven baskets, enhancing the aesthetic of the area.

4.97 out of 5 average rating, 68 reviews

Renovated Southampton Shores pool, tennis, beach

Superhost

A heated saltwater pool is framed by a spacious lawn and wooden lounge chairs. White floating orbs are seen on the water's surface, contributing to a serene atmosphere. In the background, a charming cottage with a garage door is visible, surrounded by lush greenery.

4.75 out of 5 average rating, 36 reviews

AMG-Saltwater Pool heated to November Walk2Town

The backyard showcases a serene oasis with a sparkling pool surrounded by lush greenery. A sunroom is visible, providing a view of the inviting outdoor space. The setting offers a sense of privacy, enhanced by the natural landscape.

4.95 out of 5 average rating, 95 reviews

Oasis backyard, Pool, Gym, and Sunroom!

An open living area features a large sectional sofa and a sleek dining table surrounded by several chairs. A modern ceiling fan hangs overhead, while natural light floods through skylights and large windows, enhancing the spacious ambiance of the room.

4.88 out of 5 average rating, 26 reviews

Cozy up in the Hamptons

Other fitness-friendly vacation rentals

The image captures a sparkling saltwater pool surrounded by lush green grass and shaded by large umbrellas. Comfortable lounge chairs are positioned on the pool deck, providing a relaxing outdoor space. The white exterior of the house and deck are visible in the background under a clear blue sky.

5 out of 5 average rating, 47 reviews

Sag Harbor Chic Pool Grill Gym 2Br/2Bth Dogs okay

4.94 out of 5 average rating, 17 reviews

The landscaped backyard features a heated mineral spring pool with clear blue water. Surrounding the pool are loungers and a shaded cabana with a striped canopy. Lush greenery and colorful foliage add to the serene environment.

Home in North Fork

POOL + Beach Oasis! Winter deals 2+ nights!

5 out of 5 average rating, 32 reviews

Home in West Haven

Entire house, just a walk away from the beach!

A spacious wooden deck is presented, featuring a round table surrounded by four chairs. A large umbrella stands next to the table, providing shade. Lush greenery is visible along the edges, with a pool in the background, enhancing the outdoor space.

Home in Medford

4.62 out of 5 average rating, 145 reviews

Wine Country, Hamptons, Outlets/Baseball H. Camp

A marina is visible along the calm waters of the Peconic River, featuring numerous boats docked at wooden piers. Lush greenery surrounds the area, while a few decorative flags add color to the scene. The sky shows soft hues of blue and gray, indicating early evening.

Place to stay in North Fork

4.9 out of 5 average rating, 49 reviews

The Waterfront Suite on the Peconic River 💙

Luxe

The exterior view showcases a serene pool surrounded by landscaped gardens. A spacious patio features a dining area under an umbrella, while the charming two-story structure is complemented by large windows and a manicured lawn.

5 out of 5 average rating, 16 reviews

5 Bedrms Fam Friendly Heated Pool Firepit Gym

A two-story white house with blue shutters and a welcoming front porch is surrounded by a well-maintained lawn and landscaping. The entrance features an elegant door with a decorative window, framed by a variety of shrubs and flowers that add to the inviting exterior.

5 out of 5 average rating, 27 reviews

Farmhouse Style Hamptons Beach Home, Quogue