House vacation rentals in Darien

4.91 out of 5 average rating, 146 reviews

A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.

Home in Rye

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

4.97 out of 5 average rating, 156 reviews

Home in Wilton

The Cozy Little Cottage

Charming guest apartment on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, but connected by a breezeway, and is above the garage. It is quaint and cozy, roughly 350 sq ft. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. Bedroom has a queen bed and we have a twin air mattress for use in living room.

A well-lit living room features a light-colored sofa adorned with cushions, paired with a wooden coffee table. A television is mounted on the wall, while a glass-fronted cabinet displays decorative items. Light streams through large windows, highlighting the warm wooden floor.

4.83 out of 5 average rating, 222 reviews

Gem by the water+ firepit and all fenced backyard

An episode of The Curious Case of… was filmed right here at the property. Stay where the cameras rolled and experience the same atmosphere that caught the producers’ attention. One block away from the water & 3 blocks away from Dolphin Cove. Enjoy walking and site-seeing. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. The house has also a lower-level unit.

4.91 out of 5 average rating, 178 reviews

A spacious living room featuring a comfortable sectional sofa adorned with decorative pillows. A large area rug anchors the seating arrangement, which includes two lounge chairs. Natural light filters through multiple windows, highlighting the neutral color palette and decorative wall art.

Home in White Plains

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

A bright living area is present, featuring a comfortable white sofa with blue accent pillows and a natural woven rug. A modern coffee table is placed in front, while large windows allow ample natural light. A fireplace adds a cozy focal point, complemented by a TV mounted above.

4.98 out of 5 average rating, 148 reviews

Family Cottage with 4 King Beds and Fire Pit

Escape to Norwalk Cottage, a beautifully designed 4-bedroom, 2-bath home perfect for 8 guests. This family-friendly getaway features a fully stocked kitchen, cozy fireplace, and a fun basement playroom. Relax in the private backyard with a deck, grill, and fire pit. Located on the quiet Norwalk/Westport border, you're just minutes from Calf Pasture Beach, great restaurants, and the vibrant SoNo district. Enjoy central air, fast WiFi, and a dedicated workspace for the perfect year-round escape.

4.98 out of 5 average rating, 177 reviews

A spacious outdoor area features a modern pool surrounded by wooden decking. Lounge chairs are positioned under large umbrellas, providing shade. The two-story home is visible in the background, showcasing large windows that enhance natural light.

Home in Putnam Valley

Heated Pool, Ultra Modern Home 5B, hot tub, sauna

Secluded, luxurious 5Br/3.5Bth home an hour from NYC, nested on a 9-acre property with the Appalachian trail running through. Modern-rustic design, floor-to-ceiling windows, custom kitchen, state-of-the-art appliances, balconies. Dip in the heated pool (seasonal) or the hot tub, sauna, dine alfresco from the BBQ and watch the stars. Guests can enjoy morning coffee on the private deck or evening cocoa in front of the wood-burning fireplace or the fire pit, outside, overlooking a private pond.

4.98 out of 5 average rating, 101 reviews

Family Fun! Pool, Gameroom, Yard | 5 min to Train

Welcome to our family-friendly 2-story Cape Cod! Enjoy a private fenced-in pool, game room and: - Expansive fenced backyard w/ grill + pool - Game room: foosball table w/ Roku TV - 4 bedrms: 2 king, 1 queen, 2 Twin XL - Pack&Play cribs for kids - High-Speed 1 Gig Fiber-optic internet & 2 desks - Private parking for 2 cars with additional free street parking - 3 full baths, stocked kitchen, washer/dryer, - 8min to Downtown/UConn, 5min to Train Station (50m Express to Grand Central)

A sunroom features light blue walls complemented by natural light from the large windows. Two rocking chairs are positioned beside a wooden table. Decorative mirrors reflect the cozy ambiance, while soft curtains frame the windows, providing a serene and inviting space.

4.98 out of 5 average rating, 121 reviews

Seashell Bungalow | 3 Bed 1 Bath | Beach House

Seashell Bungalow - located in Stamford, just a stone's throw from NYC. Less than a 2-minute walk from the beach. Perfect for those looking to enjoy the tranquility of the beach with the city life nearby. Outdoor dining area - perfect for summer evening relaxation. Fully equipped for fun and adventure - paddle boards and various games available. Ideal for family vacations or a friends’ getaway. Book your stay today and enjoy an unforgettable beachside adventure!

4.88 out of 5 average rating, 120 reviews

Walkable Townhouse with Garage 45 min to NYC

Please add us to your wishlist for easy access, or message us if you have any questions! -Walk to Downtown Stamford -Free attached parking garage -Minutes from the train station, I-95, and hospital -Shared backyard for relaxing, grilling, or enjoying a quiet morning coffee A relaxing and worry-free stay just minutes from everything you need, ideal for families, business travelers, or long-term guests looking for comfort and convenience.

4.94 out of 5 average rating, 137 reviews

5BR Coastal Home, Walk to Beach, Private Yard

Make yourself at home in this bright 5-bedroom getaway just a short walk from Cove Beach and Park. Enjoy a private fenced yard, game room, fire pit and plenty of ways to spend time together—whether you’re here for a family trip, weekend with friends or an extended stay. Downtown Stamford is just a few minutes away, while the beach, waterfront trails, playgrounds and recreational areas are close enough to enjoy throughout your stay.

4.96 out of 5 average rating, 356 reviews

A rustic barn-style home features a wooden exterior with multiple large windows, enhancing natural light. A spacious elevated deck is surrounded by lush greenery, while an outdoor umbrella offers shade. The setting is serene, with a glimpse of the nearby brook and wooded area.

Home in Fairfield

Beautifully Restored Barn With New England Charm

Set back from the road on one wooded acre with a brook, this renovated 4-bedroom converted barn pairs rustic New England character with modern comfort. Expect 30-foot ceilings, exposed beams, oversized windows, a babbling brook, large yard, eclectic art and furniture, a grand piano, a stocked kitchen, deck, grill, and space to gather. A memorable Fairfield stay for families, couples, small groups, beach weekends, and quiet escapes.

5.0 out of 5 average rating, 191 reviews

A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse salt pool/sauna

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Popular amenities for Darien house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 189 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

4.92 out of 5 average rating, 149 reviews

A modern farmhouse is set on a spacious lot. The architecture features a blend of dark and light siding with a white chimney. A well-maintained path leads to a front porch, surrounded by landscaped greenery, enhancing the inviting curb appeal.

Home in Sound Beach

Luxury modern farmhouse with heated pool & hot tub

4.91 out of 5 average rating, 186 reviews

A spacious living area features large windows allowing natural light to fill the room. A stone fireplace is prominently placed against a wooden wall. Comfortable seating arrangements include a large sectional sofa, with decorative plants adding a touch of greenery.

Home in Yorktown Heights

Cozy getaway 1 hr from NYC!

A spacious outdoor pool is surrounded by natural greenery, featuring a stone patio and a diving board. A covered lounge area with large windows overlooks the pool, providing a serene setting for relaxation and leisure.

4.96 out of 5 average rating, 270 reviews

Midcentury Modern ZenHouse Sculptor Studio

4.91 out of 5 average rating, 161 reviews

A dining area is presented featuring a dark wooden table surrounded by four white chairs. A decorative potted plant is centered on the table, complementing the modern decor. A doorway leads to a softly lit bedroom in the background.

Home in Port Jefferson

Port Jefferson Convenient, Cozy and Chic!

4.83 out of 5 average rating, 110 reviews

An outdoor pool area features a stone patio surrounded by vibrant flowers and greenery. Lounge chairs are arranged neatly beside the pool, and a wooden cabana is visible with a stone fireplace, creating a relaxing atmosphere for guests.

Home in Philipstown

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

4.95 out of 5 average rating, 179 reviews

A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.

Home in Cold Spring

Cozy, Modern Retreat in the Woods of Cold Spring

4.93 out of 5 average rating, 158 reviews

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

Joyful Beach House, viewing The Great South Bay

Weekly house rentals

Home in Cold Spring Harbor

A light-filled living area features a comfortable sofa adorned with nautical-themed pillows. A wooden coffee table rests on a woven rug, while a stylish floor lamp and wooden chair enhance the space. The ceiling showcases exposed beams, adding character to the room.

Nautical Farm House on Working Farm with Animals

4.86 out of 5 average rating, 315 reviews

4.97 out of 5 average rating, 270 reviews

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

Designer Beach Retreat on Exclusive Cedar Beach

4.91 out of 5 average rating, 121 reviews

Home in Bedford

Bedford Paradise Getaway | Hot Tub | Town Center

A modern kitchen and dining area are showcased, featuring sleek wooden cabinetry and a large center island with seating. Pendant lighting casts a warm glow over the dining table, while a rug adds a touch of comfort to the hardwood floor.

4.93 out of 5 average rating, 80 reviews

Fox Run 4 bedroom Private House

4.95 out of 5 average rating, 21 reviews

Historic Norwalk Home Near SoNo & NYC

4.84 out of 5 average rating, 25 reviews

A light-filled living area features a comfortable blue sofa paired with an armchair. A decorative table is topped with a vase of sunflowers and various objects. Wooden beams highlight the ceiling, while a staircase is visible in the background.

Home in Rowayton

Coastal Comfort in Rowayton, CT

4.92 out of 5 average rating, 53 reviews

The Pond House

A modern kitchen is equipped with stainless steel appliances and a large marble island. Four brown leather stools are arranged neatly at the island, illuminated by pendant lights above. Bright natural light enters through a window, enhancing the clean design.

4.96 out of 5 average rating, 48 reviews

Spacious Home Near Beach + Train Sleeps 10+ | Yard

Private house rentals

4.95 out of 5 average rating, 19 reviews

A spacious living area features exposed wooden beams and a modern fireplace, with two brown leather armchairs positioned around a coffee table. A large piece of artwork adorns the wall, complemented by a decorative fish motif above the mantel. Natural light illuminates the room.

Home in Wilton

Spectacular Renovated Barn

4.97 out of 5 average rating, 33 reviews

A welcoming living room is furnished with a large wicker sofa adorned with turquoise and white cushions. A round coffee table sits on a colorful area rug. A flat-screen TV is mounted above a decorative fireplace, while bright windows allow natural light to fill the space.

Home in Greenwich

Best hotel alternative for big group, near train

4.96 out of 5 average rating, 24 reviews

A-Frame Loft Near Metro-North | Queen + Kitchen

5.0 out of 5 average rating, 58 reviews

The living area is bright and airy, featuring a large smart TV mounted on the wall. A spacious white sofa offers ample seating, complemented by natural light streaming through the windows and stylish ceiling fan overhead.

Home in Westport

Farmhouse 1899: Minutes to Downtown Westport, CT

5.0 out of 5 average rating, 11 reviews

Home in Weston

Weston Escape, Fire Pit, Gym, Jacuzzi Tub

A spacious living area features a large sectional couch adorned with cushions, a wooden coffee table with decorative items, and a plush area rug. Natural light streams through large windows, illuminating the soft color palette of the walls and furnishings.

5.0 out of 5 average rating, 64 reviews

❤️ Your Silvermine Hideaway, nestled in nature.

5.0 out of 5 average rating, 12 reviews

A charming two-story house with blue siding and white trim is set among greenery. A spacious front porch with railings provides a welcoming entry. Lush landscaping frames the property, while a paved driveway leads to clear pathways, enhancing the inviting character of the exterior.

Home in Old Greenwich

Old Greenwich Gem