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

Total vacation rentals
Explore 120 vacation rentals in Westport

Nightly prices starting at
Westport vacation rentals start at G$12,549 GYD per night before taxes and fees

Verified guest reviews
Over 1,470 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
120 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.

Fully renovated/Walk to water & shops/fenced yard!
*Feb and Mar available for longer stays!Inquire!* *Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from quaint downtown •1 block from water •Walk to beach, restaurants, coffee, ice cream, deli & convenience store, liquor and more... • Luxe, white, 100% cotton sheets & fluffy duvets •FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue .Fiber internet for fast speed

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!

Cape on the Water
Welcome to our Cape on the Water! This unique property is located on beautiful Ash Creek, an inlet off Long Island Sound offering views of tidal wetlands, including tons of fish, bird, kayakers, paddle boarders, small sail boats etc. The house is a newly renovated Cape Cod with an open floor plan, updated Kitchen and bath rooms. Refinished oak hardwood floors through out the entire house. Large deck -great view. The house has a very cozy feel and has been also updated with brand new HVAC system.

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.

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.

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.

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.

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!

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

Nature Retreat Airbnb
House located in beautiful and tranquil Redding, CT. Two floors with private deck. Main level: half-bath, cook's kitchen with a 4-person dining area, living room with flatscreen TV with an Apple TV and a view of nature. Living room convertible couch can sleep two small children or one adult. Upstairs: 2 bedrooms with full size beds, privacy blinds, bathroom w/ shower (no tub). If you want a getaway from the city, or just an escape then come to this quiet and private house in the woods.

The Cozy Little Cottage
Charming guest apartment on our property 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, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

Stareway to Heaven
Welcome to your ideal beachside retreat in Fairfield, CT. This fully furnished 4-bedroom, 3 1/2 bath home offers an open-concept living space, a chef’s kitchen, and a private rooftop deck with stunning coastal views. Just steps from the beach and close to downtown shops and dining, it provides the perfect blend of luxury and convenience. Optional beach cruiser rentals and paddleboards are available. Flexible rental terms are offered for both short- and long-term stays.
Popular amenities for Westport house rentals
House rentals with a pool

3.5 Acres of Relaxation, Pool, & Cozy Charm

3‑Acre Weston Retreat w/ Pool & Basketball Court

Highland Colonial - Spacious Home w/ Pool

Midcentury Modern ZenHouse Sculptor Studio

Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC

Port Jefferson Convenient, Cozy and Chic!

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

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
Weekly house rentals

5 Minute Walk to Beach & Downtown Fairfield

Walk to Compo Beach Renovated Westport Home

Spacious Home Near Beach + Train Sleeps 10+ | Yard

Boho Chic Private Home in the Heart of Westport CT

Convenient and Cozy Antique Cape

Westport Gem - walk to shops, dining, town center

Private house, Walk to Beach, Train, Town, Theatre

River Cottage in Weston, CT
Private house rentals

Adorable Beach House on LI Sound

❤️ Your Silvermine Hideaway, nestled in nature.

Family friendly

Steps to Beach - Direct Water View - Pet Friendly

Spacious Coastal Escape

Entire Home in Fairfield, beach & train ~5min

Studio with kitchen and private bathroom, private door

Southport Shoreline Charm: Elegant Coastal Escape
When is the best time to visit Westport?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$105,619 GYD | G$125,696 GYD | G$99,553 GYD | G$111,893 GYD | G$126,742 GYD | G$142,010 GYD | G$149,748 GYD | G$133,435 GYD | G$120,259 GYD | G$109,592 GYD | G$115,867 GYD | G$117,540 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 |
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- Pet-friendly rentals Westport
- Rentals with a fire pit Westport
- Rentals with outdoor seating Westport
- Family-friendly rentals Westport
- Fitness-friendly rentals Westport
- Beachfront rentals Westport
- Rentals with a patio Westport
- Rentals with beach access Westport
- Rentals with a fireplace Westport
- Rentals with a washer and dryer Westport
- Rentals with pools Westport
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- Times Square
- MetLife Stadium
- Madison Square Garden
- Central Park Zoo
- New York City Center
- Yale University
- Yankee Stadium
- Columbia University
- Jones Beach
- American Dream
- United Nations Headquarters
- Rockefeller Center
- Empire State Building
- Bryant Park
- Citi Field
- Statue of Liberty
- Barclays Center
- Grand Central Terminal
- Bear Mountain State Park
- Radio City Music Hall
- Astoria Park
- Fairfield Beach
- Thunder Ridge Ski Area
- New York University





