House holiday rentals in Westport

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Top-rated house rentals in Westport

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Guest favourite

Home in Fairfield

4.9 out of 5 average rating, 118 reviews

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking

ENTIRE 2nd FL for up to 2️⃣ adult guests ONLY 2️⃣ Rooms➕Skylit Full Bath Exclusive Driveway Parking spots➕Private Main Entrance, separate from full-time renters on 1st FL using back entries Heat & Cool: wall-mounted AC➕portable Dyson ➕ Central AC w/2 sensors - host adjustable remotely TV is Screen only, works with Bluetooth & Chromecast, NO Services Kitchenette: heat/store food (NO cooking), allows affordable stay in affluent Fairfield Town Professional Clean Service Host Assistance Virtually

Guest favourite

Home in Carmel Hamlet

4.92 out of 5 average rating, 198 reviews

Lux Bungalow on the Lake

Beautiful, light flooded, waterfront home 1 hour from New York City. The 2 bedroom home is on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.

Guest favourite

Home in Rye

4.91 out of 5 average rating, 124 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!

Top Guest favourite

Home in Milford

5 out of 5 average rating, 106 reviews

HGTV renovation! Steps to shops & water | Firepit!

*Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from a quaint downtown •1 block from the water, •Walk to the beach, restaurants, coffee house, ice cream parlor, deli, convenience store, liquor store, and more... • Complete Clean Linen Participant - luxe, white, 100% cotton sheets & fluffy duvets •Relax in the FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue!

Guest favourite

Home in Fairfield

4.92 out of 5 average rating, 118 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.

Guest favourite

Home in Milford

4.96 out of 5 average rating, 234 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!

Top Guest favourite

Home in Westport

5 out of 5 average rating, 32 reviews

Westport Beach Haven - Perfect Coastal Getaway

Relax in this stunning California-style designer home in Westport. Beautifully decorated, pristine home ideally located close to Westport’s Compo Beach, train and shops. Enjoy one level open concept living, chef’s kitchen with marble counters, high-end appliances, large farmhouse dining table, two comfortable and cozy living rooms, inviting bedrooms, modern baths. Close to Westport’s wonderful restaurants, farmer’s market, downtown shops and beaches. Bonus country shed to lounge in.

Top Guest favourite

Home in Fairfield

5 out of 5 average rating, 114 reviews

Peaceful Suburban Colonial w/New Kitchen.

Looking for a clean, cozy, secluded suburban escape that's still close to great shopping, Long Island Sound, and the two Fairfield Universities? Look no further than this newly renovated colonial on a quiet tree-lined street with no through traffic. A park and basketball are just at the end of the street. Trader Joes and other great shopping are a 2 minute drive away. Sacred Heart and Fairfield U are 5 minutes away. We're right across the street in case any of us forgot anything :).

Top Guest favourite

Home in Westport

5 out of 5 average rating, 66 reviews

Westport Deco HAUS /5 min to Town /10 min to Beach

Welcome to the enchanting home of the late Jean Woodham, a celebrated sculptor renowned for her abstract and expressive works. This unique property, nestled in a serene neighborhood in Westport, harmonizes artistic charm with modern comforts, promising a distinct experience for guests seeking inspiration and relaxation. Upon entering, you're welcomed by an inviting atmosphere that mirrors Woodham's creative spirit. The space feels spacious and open, with an eclectic mix of artwork.

Top Guest favourite

Home in Newtown

4.99 out of 5 average rating, 103 reviews

Comfortable home away from home- near everything

Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

Guest favourite

Home in Danbury

4.96 out of 5 average rating, 103 reviews

Lakeview Estate - Chef's Kitchen - NYC Getaway

Stunning lake views from every angle! Gorgeous 3,200 square foot custom home with an open floor plan. Highlights include: * Chef's kitchen with Viking Range, Sub Zero Refrigerator, granite countertops & custom cabinets * Expansive 20x30 stone patio overlooking the lake with a fire-pit, speakers & outdoor lighting * 3 spacious bedrooms and 3 full bathrooms with double vanities, showers & separate bathtubs. * 5 SmartTVs including a 65" TV in the main living area

Superhost

Home in Stamford

4.84 out of 5 average rating, 172 reviews

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. 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. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.