Weston Vacation Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide.

Vacation Rentals in Weston

Adorable 1-Bedroom Cottage in Weston, CT
Fridge, microwave, oven, stovetop
Adorable 1-Bedroom Cottage in Weston, CT
10.0 out of 10, Exceptional, (24)
"Clean, Safe, and Comfortable! Thank you Jacques for the convenience of staying near Westport !"
The price is ￥30,295
per night
May 12 - May 13
Adorable 1-Bedroom Cottage in Weston, CT
DUNE Fairfield Beach
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach
3.0 star property
10.0 out of 10, Exceptional, (10)
"Modern cottage near the beach. Clean and comfortable. Very responsive."
The price is ￥28,198
per night
May 22 - May 23
DUNE Fairfield Beach
Lake Luxury
Property grounds
Lake Luxury
10.0 out of 10, Exceptional, (8)
"We loved our stay at this home. Plenty of space so we didn’t feel like we were on top of each other, gorgeous kitchen (plus a separate butler’s kitchen!), and lux bathrooms made this rental exactly what we needed. Thanks Gianna!"
Lake Luxury
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (103)
"Pleasant stay"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Westport Paradise With Every Amenity!
Outdoor pool, a heated pool
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, (12)
"Super clean, comfortable, and great for overnight stay. Will definitely be back!"
The price is ￥86,846
per night
May 13 - May 14
Westport Paradise With Every Amenity!
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Beach nearby, beach towels
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (14)
"We loved our stay at the bungalow last weekend. Donna equipped the home with everything needed for a comfortable stay, and more. It is located in a quiet area steps from the Milford Point Audubon center, Wheeler Marsh and Cedar beach. We walked to the Walnut Beach area where there are a few shops and restaurants, most notably a delicious Mexican restaurant and coffee shop. A perfect get away, despite the questionable weather."
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
Beach nearby
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
10.0 out of 10, Exceptional, (1)
"The location within walking distance church"
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
Serenity Awaits at this Cozy Lakeside Bungalow
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (15)
"We so enjoyed our stay! The house was perfect for our family, conveniently located close to extended family and with the most beautiful view. The house had everything we needed and provided the perfect home base for spring break in our hometown. We even got to experience an earth quake ;) thank you!!"
Serenity Awaits at this Cozy Lakeside Bungalow
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Fridge, microwave, oven, stovetop
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, (12)
"Stayed at Coastal Retreat for a weekend visit with son who attends Fairfield University, brought both sets of parents and teen daughter (ages ranging 73-16), plenty of room and able to enjoy a wonderful family dinner with son even in attendance. Wonderful area, close walk to beach and easy to get to downtown Fairfield and university. Very clean and welcoming! Greg was wonderful to work with and answered any question we had that came up both prior and upon arrival. The only thing we would mention...
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Direct Beachfront Property On Long Island Sound
3 bedrooms, desk, WiFi, bed sheets
Direct Beachfront Property On Long Island Sound
10.0 out of 10, Exceptional, (26)
"We had a wonderful time on the beach, in the ocean and just relaxing in the house. There were nice restaurants in the area to try and some fun day trips to take with the kids. We'd go back!"
Direct Beachfront Property On Long Island Sound
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Exterior
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
10.0 out of 10, Exceptional, (71)
"Great place to celebrate a 40th birthday. Place was clean and comfortable. Great view. Hot tub, lawn games, movie theater, pool table, and more were all great."
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
Beach nearby, sun loungers, beach towels
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
10.0 out of 10, Exceptional, (11)
"Enjoyed the house and the location! Would stay again!"
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Fridge, microwave, stovetop, coffee/tea maker
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
10.0 out of 10, Exceptional, (3)
"We went to a show at the Capital Theater and this place was very convenient. Had a nice dinner in walking distance as well. The building is old and kind of gross, but the apartment itself was very nice, modern, and clean."
The price is ￥23,304
per night
May 31 - Jun 1
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
The Safe House - High Tech Apt #2 - 3 Beds
Beach
The Safe House - High Tech Apt #2 - 3 Beds
10.0 out of 10, Exceptional, (29)
"Since it was first time with VRBO, I was a little nervous about the whole process going into it. Rob was great to answer questions and deal with both myself and my granddaughter.It was an ideal location for visiting the Hudson River Valley and along the coast to Newport. We flew into White Plains and it is just a 20 minute ride away. The apartment was clean and convenient. We only ate 3 meals in 5 days away from there. The beds were comfortable and the shower was very nice. I liked the shower...
The price is ￥16,468
per night
May 27 - May 28
The Safe House - High Tech Apt #2 - 3 Beds
The Safe House - High Tech Apt #3 - 4 beds
Beach
The Safe House - High Tech Apt #3 - 4 beds
10.0 out of 10, Exceptional, (32)
"Exactly like pictures, clean, good location for visiting friends in southern CT and spending day in the city."
The price is ￥23,770
per night
May 23 - May 24
The Safe House - High Tech Apt #3 - 4 beds
Life is Better at the Beach!
Beach nearby, sun loungers
Life is Better at the Beach!
10.0 out of 10, Exceptional, (23)
"Nice weekend with friends and young kids. The place is family friendly, clean and has a great atmosphere. Audrey and her husband were very communicative and welcoming! We loved our stay"
Life is Better at the Beach!
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Interior
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (39)
"We stayed for a second Family Christmas in a row. Stacie and Mike were great again!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Cheerful 4 bedrooms residential house.
Fridge, microwave, dishwasher, coffee/tea maker
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, (13)
"This was walking distance to the Total Mortgage Arena for our robotics competition. Having the full kitchen to cook meals was awesome. Nice comfy beds, plenty of space, I claimed the nook off the kitchen/dining area for myself. Boys had front room to work on their robot."
Cheerful 4 bedrooms residential house.
Amazing Beachfront - Dog Friendly-sorry, no cats-Classic Beach House
Interior
Amazing Beachfront - Dog Friendly-sorry, no cats-Classic Beach House
9.8 out of 10, Exceptional, (39)
"The house was great with a perfect location"
Amazing Beachfront - Dog Friendly-sorry, no cats-Classic Beach House
Sunny Studio APT above historic Westport Mill
Fridge, microwave, oven, stovetop
Sunny Studio APT above historic Westport Mill
9.8 out of 10, Exceptional, (57)
"Had a wonderful stay!!"
Sunny Studio APT above historic Westport Mill
Don't see what you're looking for?
See all available properties in Weston
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Weston you may be interested in

The Circle Hotel Fairfield
Premium bedding, desk, laptop workspace, iron/ironing board
The Circle Hotel Fairfield
3.0 star property
8.8 out of 10, Excellent, (1082)
"Quiet"
The price is ￥14,433
per night
May 14 - May 15
The Circle Hotel Fairfield
Amsterdam Hotel
Front of property
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very Good, (1500)
"The stay was very enjoyable and located in a very conscientious area."
The price is ￥15,536
per night
May 12 - May 13
Amsterdam Hotel
EVEN Hotel Norwalk, an IHG Hotel
Bicycling
EVEN Hotel Norwalk, an IHG Hotel
3.5 star property
8.4 out of 10, Very Good, (1002)
"The staff was super helpful and the amenities were very nice and accessible."
The price is ￥18,405
per night
Jun 10 - Jun 11
EVEN Hotel Norwalk, an IHG Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Search for holiday rentals in Weston on Expedia! You can easily find your home rentals, villas, holiday apartments in Weston using one of the methods below:

  • View our selection of featured holiday rentals in Weston
  • Use the map to find apartments and other holiday homes in the Weston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Weston while they last

Look no further and take a look at our great range of rental properties in Weston!

Frequently asked questions

Can I find a vacation rental in Weston?

Yes, there are vacation rentals close to well known attractions in Weston, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals that Weston has to offer?

Business or Weekend escape: This vacation home rental outside of Weston has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Weston?

Choose from 13 Expedia vacation rentals in Weston for a memorable vacation.

What’s there to see and do in Weston?

Lucius Pond Ordway / Devil's Den Preserve and Trout Brook Valley State Park Reserve are a couple of lovely local spots to get outside and enjoy nature. Wilton Historical Society and Westport Country Playhouse are a couple of places you'll find in the larger area.

What’s a vacation rental in Weston like?

Vacation rentals are private properties you can reserve for a short or long stay in Weston. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.

Recent reviews of Weston properties
Expedia verified reviews

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

5/5 Excellent
"Terrific value. "
A verified traveler stayed at Norwalk Inn & Conference Center
Posted 1 day ago
Norwalk Inn & Conference Center