Vacation rentals in Westport

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Top-rated vacation rentals in Westport

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Cottage in Westport
5 out of 5 average rating, 77 reviews

Wild Rose Cottage (Westport, CT)

Luxurious newly-renovated Cottage in prime location in Westport's historic district. Studio with queen-sized bed, kitchen (w/fridge, dishwasher, stove, oven, toaster, Keurig), full bathroom, A/C, fireplace, W&D, TV, WiFi (w/Amazon Fire Stick). Parking for one car. Back-up generator. Within stone's throw of Hudson Malone, Outpost Pizza, Merritt Country Store, Coffee An' Donut Shop and Grapevine liquor store. Just a short stroll on the sidewalk to downtown Main Street's shops and restaurants.

Top guest favorite
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
4.96 out of 5 average rating, 348 reviews

Luxurious Barn With New England Charm

Three decades of tasteful renovations — many using re-purposed material — have rendered this converted barn magazine-worthy. Set-back from the road on 1-acre of wooded land with a babbling brook, this conveniently-located modern home maintains its rustic allure. With 30-foot ceilings, exposed wooden beams, dozens of windows, an array of eclectic furniture, and a grand piano, the charm of the barn is immediately obvious. Perfect for romantic getaways, small retreats, family gatherings, and more.

Top guest favorite
A spacious living area features a dark sofa and a patterned armchair, offering comfortable seating. A wooden Murphy bed is folded against the wall, while a small table with a lamp and decorative flowers adds to the inviting ambiance. Large windows provide natural light.
Guest suite in Fairfield
4.94 out of 5 average rating, 453 reviews

Private Studio Apartment; Kitchen; Fully Furnished

This 625 sqft fully furnished studio apartment has its own private entrance and sleeps 2-3 with a queen bed and Murphy bed. Other than outside, there is no contact with other people (hosts, other guests, etc) possible unless the guest allows such. The unit consists of a living room, dining space (breakfast basics provided), kitchen, full bathroom/laundry. Walk to Fairfield U; an easy train ride to NYC. (Need the Murphy bed? PLEASE do not wait until just before checkin to let us know that!)

Top guest favorite
The living area features a blend of classic and modern decor, including a comfortable sofa and elegant armchairs around a richly patterned rug. A brick fireplace adds warmth, while a television is positioned in front of the seating area. Natural light fills the space from large windows.
Apartment in Westport
4.92 out of 5 average rating, 314 reviews

Spacious Westport Apt surrounded by nature!

Spacious mother-in-law basement apartment with private entrance that opens to the backyard. Large windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space for up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, hikes, wonderful bakeries and restaurants.

Top guest favorite
A cozy seating area features a wooden chair with a green cushion. Natural light floods in through the glass doors adorned with light yellow curtains, offering views of the garden outside. A patterned rug adds warmth to the space.
Cabin in Norwalk
4.94 out of 5 average rating, 104 reviews

Sunny French Cottage

This unique, sunny cottage has it's own style. Private and peaceful, completely renovated cottage with French vibes. Originally used as a painting/design studio. It is an ideal place to relax and enjoy the surrounding nature. The upstairs bedroom is loft style and has a luxurious queen size bed. It's ideal for short and long stays. It is a perfect place for cozy evenings and lazy mornings, it can also serve as a temporary workplace. High tea style, organic breakfast available (20$ per person)

Top guest favorite
Guesthouse in Rowayton
4.99 out of 5 average rating, 161 reviews

1BR full cottage, 1 min walk to private beach

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian and dog friendly town; you don't even need a car while here.

Top guest favorite
Home in Wilton
4.97 out of 5 average rating, 149 reviews

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.

Top guest favorite
A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.
Cottage in Weston
4.97 out of 5 average rating, 217 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Superhost
Apartment in Westport
5 out of 5 average rating, 3 reviews

Downtown Westport CT Studio

Situated in a prime location that is walking distance to downtown, with a variety of restaurants, numerous designer brand stores, and entertainment venues such as the Levitt Pavilion for Performing Arts. Right of off the Merritt Parkway, I-95, and Westport train station, 10 minutes from Longshore Golf Country Club, Compo Beach, and Sherwood Island State Park. Relax in the homey yet spacious studio with private entrance and patio, in unit laundry, and open floor plan.

Top guest favorite
A quaint cottage is nestled among vibrant trees, showcasing rich foliage in shades of green and burgundy. A well-kept lawn surrounds the cottage, with a white door framed by flower beds. The serene setting invites relaxation in a natural environment.
Cottage in South Salem
4.96 out of 5 average rating, 270 reviews

Private cottage in horse country &1 hour from NYC!

Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)

Top guest favorite
The bedroom features a queen size spindle bed with quality bedding, flanked by two nightstands with lamps. A dedicated work desk is equipped with a lamp and USB ports. Shelving adds storage, while a small seating area is present, illuminated by natural light from the windows.
Apartment in Fairfield
4.98 out of 5 average rating, 180 reviews

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

Guest favorite
A spacious game area features a well-maintained pool table at its center. Soft lighting enhances the neutral-colored walls, while a lounge area with a chair and smart TV can be seen in the background, offering a welcoming environment for leisure activities.
Apartment in Westport
4.88 out of 5 average rating, 230 reviews

Spacious Studio with Pool Table

Escape to your private Westport studio retreat in one of the most desirable neighborhoods in town! This stylish space comfortably sleeps 2 guests and is perfect for fun and relaxation. Unwind with your own private pool table, a cozy home theater, and a dedicated workspace. Centrally located between Compo Beach and Downtown, it's the ultimate getaway for couples or small groups seeking a unique and entertaining stay.

Popular amenities for Westport vacation rentals

When is the best time to visit Westport?

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Frequently Asked Questions

  • Where should I stay in Westport?

    Make yourself at home in Westport by choosing from our most frequently booked neighborhoods. We have over 250 vacation rentals in Saugatuck, over 180 vacation rentals in Greenfield Hill, and over 130 vacation rentals in Greens Farms.

  • Are there vacation rentals with a dedicated workspace in Westport?

    Yes! Work meets play with ease at over 100 vacation rentals in Westport featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Westport?

    Four-legged friends are welcome in Westport. Choose from more than 70 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in house rentals in Westport?

    Experience the best of Westport with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Westport vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Westport, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Westport have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Westport. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Westport have wifi?

    Absolutely! We offer over 120 house rentals with wifi in Westport. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Westport have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Westport. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Westport have a gym?

    Absolutely! We offer over 30 house rentals with a gym in Westport. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Westport?

    Westport has more than 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about vacation rentals in Westport

  • Total vacation rentals

    Explore 150 vacation rentals in Westport

  • Nightly prices starting at

    Westport vacation rentals start at €52 per night before taxes and fees

  • Verified guest reviews

    Over 3,480 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Westport vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Westport rentals

  • 4.9 Average rating

    Westport stays are highly rated by guests—averaging 4.9 out of 5!