
House vacation rentals in Westport
Find and book unique houses on Airbnb
Quick stats about house rentals in Westport

Total vacation rentals
Explore 110 vacation rentals in Westport

Nightly prices starting at
Westport vacation rentals start at G$14,644 GYD per night before taxes and fees

Verified guest reviews
Over 1,530 verified reviews to help you choose

Family-friendly vacation rentals
100 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
110 of Westport vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Westport rentals

4.9 Average rating
Westport stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Westport
Guests agree: these houses are highly rated for location, cleanliness, and more.

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
4.97 out of 5 average rating, 154 reviews
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
4.91 out of 5 average rating, 144 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
4.94 out of 5 average rating, 143 reviews
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
4.91 out of 5 average rating, 176 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
5.0 out of 5 average rating, 57 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
4.98 out of 5 average rating, 142 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
4.97 out of 5 average rating, 156 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
4.97 out of 5 average rating, 270 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
4.99 out of 5 average rating, 190 reviews
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
4.94 out of 5 average rating, 108 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!
LocationFamilyBeach
4.97 out of 5 average rating, 115 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
4.94 out of 5 average rating, 145 reviewsPopular amenities for Westport house rentals
House rentals with a pool

Luxury modern farmhouse with heated pool & hot tub
LocationFamilyCheck-in
4.92 out of 5 average rating, 145 reviews
Port Jefferson Convenient, Cozy and Chic!
ValueFamilyNearby
4.93 out of 5 average rating, 157 reviews
Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
ValueLocationAccuracy
4.88 out of 5 average rating, 129 reviews
Midcentury Modern ZenHouse Sculptor Studio
ValueFamilyAmenities
4.96 out of 5 average rating, 269 reviews
3‑Acre Weston Retreat w/ Pool & Basketball Court
ValueFamilyCleanliness
5.0 out of 5 average rating, 29 reviews
Harbor House Stony Brook Village
FamilyValueAccuracy
5.0 out of 5 average rating, 14 reviews
Casa la Lazy | 3 BDRM | 1.5 Bth | Pool | BBQ
LocationFamilyPets
5.0 out of 5 average rating, 12 reviews
Serenity in Weston - House, barn & pool
LocationFamilyNearby
4.93 out of 5 average rating, 14 reviewsWeekly house rentals

Walk to Compo Beach Renovated Westport Home
LocationValueBreakfast
5.0 out of 5 average rating, 58 reviews
Stareway to Heaven
FamilyLocationSleep quality
5.0 out of 5 average rating, 62 reviews
Westport Gem - walk to shops, dining, town center
ValueLocationSleep quality
4.89 out of 5 average rating, 35 reviews
Spacious Home Near Beach + Train Sleeps 10+ | Yard
FamilyLocationCheckout
4.96 out of 5 average rating, 46 reviews
Westport CT In Town, Private
LocationFamilyDecor
4.91 out of 5 average rating, 23 reviews
Boho Chic Private Home in the Heart of Westport CT
LocationFamilyCleanliness
4.89 out of 5 average rating, 18 reviews
Westport Luxury Escape | 10 Minutes to Beach
FamilyLocationAmenities
5.0 out of 5 average rating, 96 reviews
Southport Shoreline Charm: Elegant Coastal Escape
ValueLocationSleep quality
4.81 out of 5 average rating, 145 reviewsPrivate house rentals

Spectacular Renovated Barn
LocationFamilyCondition
4.94 out of 5 average rating, 17 reviews
Family friendly
FamilyValueSleep quality
4.95 out of 5 average rating, 60 reviews
Fairfield’s Four bedroom Family Home
FamilyLocationCondition
5.0 out of 5 average rating, 25 reviews
Magical Weston Retreat
ValueFamilyDecor
4.9 out of 5 average rating, 78 reviews
Nice Colonial, EV Charger, Patio BBQ, SoNo, Beach
LocationFamilyCleanliness
4.94 out of 5 average rating, 18 reviews
Beach House with Private Beach
LocationFamilyHospitality
4.95 out of 5 average rating, 20 reviews
Salt & Blue | Walk to Beach & Tyde •4BR• Fire Pit
FamilyLocationIndoor spaces
5.0 out of 5 average rating, 31 reviews
The Pond House
LocationFamilyHospitality
4.92 out of 5 average rating, 52 reviewsWhen is the best time to visit Westport?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$105,648 GYD | G$125,732 GYD | G$99,581 GYD | G$102,928 GYD | G$129,706 GYD | G$151,673 GYD | G$149,790 GYD | G$133,472 GYD | G$120,292 GYD | G$109,623 GYD | G$115,899 GYD | G$117,573 GYD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Destinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Boston Vacation rentals
- Ocean City Vacation rentals
- Jersey City Vacation rentals
- Portland Vacation rentals
- Newark Vacation rentals
- Baltimore Vacation rentals
- Atlantic City Vacation rentals
- Newport Vacation rentals
- Providence Vacation rentals
- Times Square
- Central Park Zoo
- Yale University
- Jones Beach
- Columbia University
- Yankee Stadium
- American Dream
- MetLife Stadium
- New York City Center
- Rockefeller Center
- United Nations Headquarters
- Empire State Building
- Bear Mountain State Park
- Bryant Park
- Barclays Center
- Citi Field
- Statue of Liberty
- Grand Central Terminal
- Brooklyn Bridge
- Radio City Music Hall
- Astoria Park
- Fairfield Beach
- Thunder Ridge Ski Area
- The Metropolitan Museum of Art





