Top 10 Airbnb Vacation Rentals In Westport, Connecticut - Updated 2023


Westport, Connecticut is a town that blends traditional looks and culture with a modern zest. Located along the Gold Coast, it’s not only home to plenty of sandy beaches but also green hills and lakes. Historic neighbourhoods such as Saugatuck or Old Hill are teeming with a history that’s just waiting to be explored, while Downtown Westport is lively, with shophouses and restaurants all around. There’s something for every traveller here, be it a peaceful getaway in a farmhouse, an exciting vacation in a studio near the beach or a family trip to spend some time together. Read on to find the best Airbnb vacation rentals in Westport, Connecticut!

1. Modern studio atop historic mill (from USD 79)

If you ever wanted to live in a studio apartment that’s sleek and modern yet has historical roots, this is your chance. Located atop a renovated mill, this studio is bright, well-furnished and beautifully decorated with hardwood floors and plenty of skylights. From the house, you’ll be able to catch views of the Sasco River down below and also hear the streams of water from the nearby waterfall.

For those who need to get some work done during their trip, there’s high-speed Wifi available. There’s even a co-working space downstairs near the mill that all guests have free access to. And after getting that work done, head out to Lighthouse Point, which is 2 miles (3.2 kilometres) away, to catch the sunset.

Sunny Westport Studio Apt. Above Historic Mill
Westport, Connecticut, United States
175 reviews Superhost  Wifi Available
Entire rental unit 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the beds and furniture are really comfortable
exceptional studio apartment with great amenities and nice touches like extra towels linens and bottles of water
the beds and linens are very comfortable - even the sofa bed was comfortable
nice set-up with alexa for music etc and everything you need for comfortable stay
the furnishings are fun and funky the bed very comfortable and the kitchen had everything i needed
really clean and neat
the apartment was incredibly clean and stylish
spotlessly clean well appointed perfectly situated
the studio is bright clean and spacious
very clean and host super helpful
great hosts
the host was very helpful and provided excellent service and attention to detail
host are amazing and very helpful
gerard is the greatest host ever very professional all requests handled and service was amazing the rental was also amazing
gerard is a great host and always available
and close to charming downtown fairfield
the location is convenient and safe
the location is great and convenient for whatever you need
the location of perfect and close to anything you might need or want
this studio apartment is so adorable the location is great because there is trader joe’s and terrain close by
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2. Bright and airy studio home (from USD 120)

For this house, you wouldn’t even need to install any lightbulbs because the natural lighting makes it so bright and airy already. With a plethora of windows and skylights, you also get a ton of views of the mill and pond outside. The furniture feels contemporary and was designed to celebrate artists like Van Gogh.

You’ll be surrounded by an endless amount of trees, flowers and animals during your stay. Take a trip down to the pond and the woods nearby and view some of the mallards, egrets or swans in their natural homes.

Sunny Westport 2 BR Retreat above Historic Mill
Westport, Connecticut, United States
218 reviews Superhost  Wifi Available
Entire rental unit 3 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
amazing kitchen (bonus- the view from the kitchen was so tranquil) comfortable beds
the kitchen is a beautiful full working kitchen
we had access to smart tvs during our stay
the added beehive work space and conference rooms are great if you have a business meeting
great property but bathroom small
it was impeccably clean and also stylish
an incredibly clean and delightful place
super clean and tons of great little details
i very clean and beautifully decorated place to stay
it was so clean we wondered if nobody had ever been there before
site staff responsive and professional
splendid stay excellent host
the host went above and beyond to make sure our stay was perfect
outstanding host and an amazing space
this place was wonderful the host was truly amazing
the location was great too
the location is superb with direct access to 95 train stations shopping and beaches
location was wonderful and was within a short drive of all our activities
the location was great with easy access to main roads but also some walkable restaurants etc
great location everything was easy and made our stay so pleasant
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3. Newly renovated cottage (from USD 207)

This house is aptly called Cottage 1790 and was renovated to reflect how traditional houses of the 18th century looked. You’ll get a mixture of traditional and modern, with a rustic fireplace as well as a comfortable queen-size bed. The kitchen is fully equipped with pots, pans, a fridge and even a dishwasher, while the garden outside contains a large barbeque grill and a terrace.

The house is also centrally located, being 50 minutes away from New York City, 20 minutes away from the town of Yale and is also very close to the sea.

Cottage c. 1790 in Westport, CT 50 min da New York
Westport, Connecticut, United States
30 reviews  Wifi Available
Entire cottage 4 Beds 5 Guests 3 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
the three of us were very comfortable with ample space and enzo & jennifer were great hosts
hospitable hosts clean and comfortable house
host provided quick and courteous responses
great place and great host
lorenzo was an amazing host to our friends
lorenzo was the perfect host and was very quick with responding to my questions
lorenzo is an awesome host and we would highly recommended his place to others
lorenzo’s place is super comfortable and close to everything
really enjoyed the location and the space
great location easy access to merrit parkway local stores and amenities
Read more reviews

4. Conveniently located home with a garden patio (from USD 50)

Make yourself at home with this accommodation that has very welcoming vibes. From the outside, it may not look like much, but on the inside, it is equipped with anything a traveller might need on their stay. The kitchen area is clean and has a stove so you can do all your cooking and a fridge to store food in. The living room has a comfy sofa, only rivalled by the fluffy bed in the bedroom. The outside patio is the best place for you to catch some fresh air.

Situated away from the train station by a 15-minute walk, this accommodation is an affordable choice to connect yourself with the city around you.

room ,near station train ( 15 min walking),nice
52 reviews  Wifi Available
Private room in home 1 Bed 1 Guest 1 Bedroom 1 Bathroom

Accommodates: 1

Top guest reviews
Amenities & Room:
nice comfortable place to stay
if that doesn't bother you the room is otherwise clean comfortable quiet and the host very pleasant
janette was a great host
humble nice and kind host
great experience host makes an effort to make you feel like you have the place to yourself
janette is very welcoming and friendly
nice quiet room walking distance to lots of stores bus train
the house is in a safe location
great access to shops and restaurants nearby
Read more reviews

5. Cottage with a panoramic view of a relaxing pond (from USD 486)

Situated on a private street, this two-storey cottage has three bedrooms and a view to die for. Overlooking Mill Pond, you’ll wake up to and be greeted by the delightful sounds of the aquatic animals and birds roaming the pond. Not to mention the warm, angelic natural light that enters the accommodation through the open kitchen, dining room and living room. Guests can head to the upper deck, which makes a perfect viewing area and relaxing spot.

Aside from the short walk to Mill Pond, you can also walk an extra 0.5 miles (800 metres) and reach Mill Pond Beach, a quiet, tranquil and peaceful spot. If you want more action, head to Compo Beach - a three-minute drive away - for more restaurants and shops to explore.

Mill Pond Retreat
Westport, Connecticut, United States
51 reviews Superhost  Wifi Available
Entire cottage 4 Beds 6 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
great wifi and televisions with cable channels were much appreciated
the view is absolutely amazing every amenity you could ask for and enough room for our family
the place was clean quiet and peaceful
second lj’s home was sparkling clean extremely well appointed and cozy
the house was very clean and had such amazing views
the home was spotless exactly as represented and perfectly located for what we wanted
host is very kind and helpful
i highly recommend this home and host
laurajean was the most wonderful host and responded to messages immediately she made us feel so welcome
laurajean was super helpful and went out of her way to make sure we had the best experience
laurajean is a fantastic host and her home is truly a special place
excellant location close to everywhere great value
great spot close to everything very tranquil
the location is perfect for enjoying all of the best of westport
it is a great place to spend a weekend
amazing location with fantastic views
Read more reviews

6. Redecorated barn near the beach

This guest barn was decorated by the host to ensure the comfiest and most luxurious stays to all travellers. With a bunk bed and a queen-size bed in the loft, it’s perfect for families who want to bring their kids out for a vacation. The accommodation is cosy and warm, and there’s also a garden that’s managed by the owner right outside.

Old Mill Pond Beach is a 10-minute walk away if you want to catch some rays or swim on the beach. Other nearby attractions include Compo Beach, Longshore Golf, shopping spots and restaurants in Downtown Westport.

Guest Barn at Old Mill Pond Beach
Westport, Connecticut, United States
37 reviews
Entire bungalow 3 Beds 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
a bit cozy to entertain it is the perfect size for sleeping and one's morning coffee
the beds including the bunk beds were some of the most comfortable we've encountered in an airbnb
very private very cozy and very clean
very clean and the hosts were welcoming and attentive
ed is a very nice host
he and buddy were great hosts
ed was super welcoming and attentive
ed and buddy are great hosts
ed is a great host and very friendly
this is a very well located place a short drive or walk to the beach
beautiful little house in westport walking distance from the closest place
the barn is wonderful and it's location is top notch
just a 10 min walk to the beach it's the perfect getaway
ed’s place is great and we loved being so close to the beach
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7. Charming farmhouse for large groups

This farmhouse accommodation looks like something straight out of a movie. With an antique look and charming feel to it, the white-painted exterior makes it very welcoming for guests. Moreover, the space can be modified to have up to four bedrooms for seven guests, making it the perfect house for big families or large groups of friends.

Better yet, the beach is only a mile (1.6 kilometres) away, meaning that you can get some fun in the sun at your convenience. If you want to head out on a longer trip, it only takes an hour to get to New York City.

Westport Farmhouse Sleeps 4+
Westport, Connecticut, United States
34 reviews
Entire house 4 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
wifi speed was good in all parts of the place
the place was clean and comfortable with wonderful amenities including coffee
comfortable a little tight for two couples but it worked out well
the beds and sofa are very comfortable the feeling in the home is warm and inviting
ronald's house is clean and charming
fantastic rental in every way cozy stylish and super clean and all for an excellent price
ron is a wonderful host
she’s friendly and a good neighbor
ronald was very responsive and accommodating when i asked for the possibility of an early check-in
ron was a great host: super accommodating excellent communicator and flexible
the location is great
great location convenient to everything
proximity to the highway and train station was good and inside you could not hear either
this place is a gem great location super comfortable and roomy
easily accessed via i-95 and very close to the train station
Read more reviews

8. Beautiful fairytale-like cottage

If you want to experience a fairytale-like stay, choose this old cottage surrounded by trees, grasslands and a flowing river. Walking across a small bridge will bring you to your new home that screams rustic yet charming. On the porch, you can watch all the animals that roam across the spacious land, and in front of the stone fireplace, you and your family can gather together for a peaceful night.

It’ll be hard to leave the tranquillity of this space, but there are still restaurants and a beach nearby if you’d like to. It’s also an hour’s drive to New York City in case you want to visit this bustling metropolis.

Enchanting Storybook Cottage
Westport, Connecticut, United States
39 reviews
Entire cottage 3 Beds 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
the house had all the little things for a great stay: complete kitchen washer dryer roku extra linens/towels
comfortable beds and furniture helped to make this a very relaxing retreat
quiet serene and comfortable
beautiful cute cottage on huge grounds our stay with 2 young kids was magical and super comfortable
the great room and dining area allowed me to host a family lunch comfortably
beautiful home and very clean
nice clean and quiet
the house was spotless & super cozy
everything was great super clean space
the house was sparkling clean and beautifully appointed
steven was very communicative and a trustworthy host
steven was also super responsive regarding any questions we had
the hosts were immediately responsive to any issues
the hosts were all so accommodating and thoughtful even bringing over bagels and treats for us
steven and laurajean were amazing hosts first and foremost
located perfectly near downtown westport with shops and restaurants
this place was an amazing location in a beautiful town near the beach and plenty of great restaurants
close to a bunch of delicious places to eat
best for getaway from the city and close to supermarket
the location is perfect as it is close to both the merritt and 95
Read more reviews

9. Victorian-style farmhouse near villages and beach

This farmhouse is modelled after those in Victorian times, carrying a traditional and classic feel. The furniture is carefully chosen in bright, beige and pastel colours. Combined with the natural lighting from the windows, it makes the entire space feel so much lighter. Not to mention the comfy queen-size bed with fluffy sheets.

Guests can also head to nearby attractions, including Levitt Pavilion, Compo Beach or Saugatuck Village - all within walking distance. You can also explore the massive grounds around the property to enjoy nature and relax.

Victorian Farmhouse Between Town and Beach
Westport, Connecticut, United States
38 reviews
Private room in house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the bed and room were comfortable with air conditioning available
the room itself is lovely and full of natural light impeccably clean
the room was private and comfortable
we had a great comfortable set up and had a lot of privacy
we both immediately felt comfortable and warmly welcomed
clean and perfect hospitality
the space was clean comfortable and a solid place to stay
the bathroom was bright and clean with higher-end products and soft towels
the room itself is spacious and clean and the bed is comfortable— i slept so well
the room and the bathroom are very clean and comfortable i had a very nice and restful time there
she was easy to communicate with thoughtful and kind
christine is a great host she's quick at responding very accommodating and made us feel right at home
christine was an excellent host and made my stay at her rambling victorian westport home very enjoyable
the room is great and christine is a courteous host
christine is a delightful host and the space was more than i expected
it's a good location too
they loved the location and quietness after traveling many miles
the location is great as it is near town and the beach
we really enjoyed our stay at christine's place
we absolutely enjoyed our stay at christine’s place
Read more reviews

10. Peaceful studio with meditative grounds

This accommodation was built all the way back in 1806, over two centuries ago. But don’t let the age fool you because it has been renovated and furnished with the latest furniture and gadgets. The bathroom is fully equipped with a bathtub and a shower. The kitchen has a microwave, a fridge and a coffeemaker for you to whip up some meals. Surrounding the house itself are unique art pieces that will definitely intrigue you.

For a more peaceful and tranquil getaway, the meditative grounds are right next to you. Find some zen at the copper beech tree that’s 300 years old, or at the ponds, gardens and sculptures nearby.

Unique MidCen Mod Studio on 1806 Estate, Retreat
Westport, Connecticut, United States
62 reviews Superhost  Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
good size room with bed and couch area
check in/out was easy the studio was very stylish and the mattress was especially comfortable
the bed--that memory foam mattress---was the best i will stop again when i am in the area
the adaptation to an innovative/limited “kitchen” was a challenge but never any difficulty
we had a wonderful stay at the studio the room was charming and cozy
everything was very clean
the room was clean and comfortable
it is also very clean and well-decorated
it is clean quiet private and so comfortable
thoughtful details were left throughout studio and place was very clean
jeanine & frederic were wonderful hosts
gracious host and lovely setting
frederic and jeanine are wonderful hosts attentive to every detail and very responsive
jeanine and frederic are wonderful hosts
a lovely stay the perfect hosts
cute place perfect location for us
great location with easy access to surrounding town and train station
good location if you are traveling around fairfield county
although close to attractions restaurants and shopping the property is a quiet retreat
it was close to downtown westport and far enough away that it felt like a retreat
Read more reviews

Plan your next trip to Westport, Connecticut now

With sandy shores, peaceful grasslands and tranquil rivers and lakes, Westport is the perfect town for any sort of traveller. Whether you’re with your family, friends or significant other, there’s plenty to enjoy in this small town on the coast of the United States. From barns and farmhouses to Victorian-era studios and cosy apartments, use this list to find the best Airbnb vacation rentals in Westport, Connecticut!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Born in Hanoi and moved across London to Sydney to Singapore - I'm your typical starry-eyed student with a heart to explore the world, just one who's too poor to travel but does so anyway.

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