House vacation rentals in Westport

4.97 out of 5 average rating, 154 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.

FamilyLocationQuiet

4.91 out of 5 average rating, 144 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!

FamilyLocationCheck-in

The living area features a dark grey sofa adorned with decorative pillows, positioned on a textured area rug. A small wooden side table stands next to the sofa, and a framed landscape artwork hangs on the wall. A dining area is visible through the doorway.

4.94 out of 5 average rating, 143 reviews

Downtown Fairfield 3 bedroom Colonial

Enjoy a charming, 3 bed/2 full bath Colonial that is only a 4 block walk from the coffee shops, bars, and restaurants on the Post Road and .7 mile from the Fairfield Train Station. The house is over 1500 sq. feet on a quiet street and only a mile to the town beaches. Work has taken me from Fairfield, but it remains home, so the house is fully stocked with everything. If you're into shooting hoops, you'll like the lined and paved court. Small well-trained dogs and longer stays are negotiable.

LocationFamilyKitchen

4.91 out of 5 average rating, 176 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!

LocationFamilyKitchen

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.

5.0 out of 5 average rating, 57 reviews

Farmhouse 1899: Minutes to Downtown Westport, CT

Welcome to Farmhouse 1899. This old house is full of charm and history and is the perfect mix of old and new. Every inch of this home has been meticulously designed and furnished by a NYC real estate professional intent on recreating a 19th century farmhouse vibe for today’s modern family. Enjoy easy access to everything from this centrally located home. Close to 2 major highways, a 10 minute walk or 3 minute drive to Downtown Westport where you can enjoy great shops, restaurants and nightlife.

ValueFamilyAccuracy

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, 142 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.

LocationFamilyDecor

A vibrant sunset fills the sky with hues of pink, orange, and purple, reflecting on the tranquil water. Silhouettes of two birdhouses are visible on posts in the foreground, framed by lush vegetation along the shore.

4.97 out of 5 average rating, 156 reviews

3 Bedroom Beach House with Hot Tub!

Enjoy breathtaking sunset views in our spacious beach house while dining or relaxing in the hot tub. Snuggle up in front of the fireplace while watching a movie on the frame TV. Wake up in the master suite to spectacular marsh views while listening to birds from the Audubon Society. Steps to a white sand beach, heated bathroom floors, luxury bathrobes, linens, and organic mattresses. 6-bikes for exploring. A true resort-like experience with a chef's kitchen making a home away from home.

FamilyLocationHeating

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.

4.97 out of 5 average rating, 270 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

ValueFamilyGetting around

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.

4.99 out of 5 average rating, 190 reviews

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

FamilyLocationView

4.94 out of 5 average rating, 108 reviews

Home in Stamford

5BR Beach House, Game Room + Huge Backyard

Escape to this spacious 5-bedroom Shippan beach home, designed for families and groups to relax, reconnect and have fun together. Just a short walk from West Beach, the home features a huge private fenced backyard, two large decks, fire pit, game room, pool table, ping pong, foosball and plenty of indoor and outdoor space for everyone to spread out Located just minutes from Downtown Stamford and Metro-North, it’s an ideal home base for family getaways, group stays and corporate retreats

LocationValueCleanliness

4.97 out of 5 average rating, 115 reviews

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.

Home in Stamford

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!

LocationFamilyBeach

4.94 out of 5 average rating, 145 reviews

Oceanfront Beach House w/ Private Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

LocationValueSleep quality

Popular amenities for Westport house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 145 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

LocationFamilyCheck-in

4.93 out of 5 average rating, 157 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!

ValueFamilyNearby

4.88 out of 5 average rating, 129 reviews

A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.

Home in Hamden

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

ValueLocationAccuracy

4.96 out of 5 average rating, 269 reviews

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.

Home in Stamford

Midcentury Modern ZenHouse Sculptor Studio

ValueFamilyAmenities

5.0 out of 5 average rating, 29 reviews

Home in Weston

3‑Acre Weston Retreat w/ Pool & Basketball Court

ValueFamilyCleanliness

5.0 out of 5 average rating, 14 reviews

Home in Stony Brook

Harbor House Stony Brook Village

FamilyValueAccuracy

A spacious outdoor area features a glistening pool surrounded by multiple lounge chairs and large umbrellas. A wooden deck leads to a relaxing seating area with comfortable couches, providing ample space for gatherings. Lush greenery is visible in the background, adding a sense of privacy.

5.0 out of 5 average rating, 12 reviews

Casa la Lazy | 3 BDRM | 1.5 Bth | Pool | BBQ

LocationFamilyPets

4.93 out of 5 average rating, 14 reviews

Home in Weston

Serenity in Weston - House, barn & pool

LocationFamilyNearby

Weekly house rentals

5.0 out of 5 average rating, 58 reviews

Walk to Compo Beach Renovated Westport Home

LocationValueBreakfast

The exterior of the modern beachside retreat is showcased, highlighting a three-story structure with balconies on the upper floors. The light-colored facade is complemented by stone accents and landscaped lawn, providing a welcoming entryway. Nearby streets and neighboring homes create a quaint coastal neighborhood ambiance.

5.0 out of 5 average rating, 62 reviews

Stareway to Heaven

FamilyLocationSleep quality

The spacious kitchen features white cabinetry and dark granite countertops. A central island with seating for two is present. Large windows provide ample natural light and views of the outdoor greenery. Appliances include a microwave, stove, and dishwasher, contributing to a fully equipped cooking space.

4.89 out of 5 average rating, 35 reviews

Westport Gem - walk to shops, dining, town center

ValueLocationSleep quality

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, 46 reviews

Spacious Home Near Beach + Train Sleeps 10+ | Yard

FamilyLocationCheckout

A well-maintained backyard with lush green grass is surrounded by mature trees. A wooden deck is furnished with several white lounge chairs, offering a comfortable outdoor gathering space. The house features large windows that provide a view of the yard.

4.91 out of 5 average rating, 23 reviews

Westport CT In Town, Private

LocationFamilyDecor

A serene outdoor scene showcases a stone Buddha statue partially surrounded by a light dusting of snow. The statue is positioned near a tree, with green foliage peeking through the snow on the ground. Soft sunlight highlights the peaceful setting.

4.89 out of 5 average rating, 18 reviews

Boho Chic Private Home in the Heart of Westport CT

LocationFamilyCleanliness

5.0 out of 5 average rating, 96 reviews

Westport Luxury Escape | 10 Minutes to Beach

FamilyLocationAmenities

A welcoming living area features a comfortable gray sofa and two armchairs. A wooden coffee table sits in the center, accompanied by a decorative candle arrangement. Light-colored walls are complemented by large windows, allowing natural light to illuminate the space.

4.81 out of 5 average rating, 145 reviews

Southport Shoreline Charm: Elegant Coastal Escape

ValueLocationSleep quality

Private house rentals

4.94 out of 5 average rating, 17 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

LocationFamilyCondition

The exterior of a two-story house is displayed with a traditional design featuring white siding and black trim. A welcoming front porch is flanked by neatly landscaped flower beds. A well-maintained lawn surrounds the property, with a driveway visible in front.

4.95 out of 5 average rating, 60 reviews

Family friendly

FamilyValueSleep quality

5.0 out of 5 average rating, 25 reviews

Fairfield’s Four bedroom Family Home

FamilyLocationCondition

4.9 out of 5 average rating, 78 reviews

A charming two-story home is set against a backdrop of autumn foliage. The exterior features white siding with a red door, large windows, and landscaped gardens. A path leads to the front entrance, while a spacious lawn surrounds the house, offering a tranquil setting.

Home in Weston

Magical Weston Retreat

ValueFamilyDecor

4.94 out of 5 average rating, 18 reviews

Nice Colonial, EV Charger, Patio BBQ, SoNo, Beach

LocationFamilyCleanliness

The three-story coastal retreat features a charming blue exterior, punctuated by multiple windows that allow natural light in. The covered parking area is located beneath the elevated structure, with a welcoming front door painted in a vibrant teal. An American flag is displayed near the entrance.

4.95 out of 5 average rating, 20 reviews

Beach House with Private Beach

LocationFamilyHospitality

5.0 out of 5 average rating, 31 reviews

Salt & Blue | Walk to Beach & Tyde •4BR• Fire Pit

FamilyLocationIndoor spaces