Weston Vacation Rentals

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Vacation Rentals in Weston

Fridge, microwave, oven, stovetop
Adorable 1-Bedroom Cottage in Weston, CT
10.0 out of 10, Exceptional, (25)
"Everything was extremely lovely. The location is so beautiful and the house is very quaint and cozy, loved it!"
The price is CA $266
CA $414 total
includes taxes & fees
May 28 - May 29
Adorable 1-Bedroom Cottage in Weston, CT
Exterior
Stamford Suites
2.5 star property
7.0 out of 10, Good, (711)
"Not a bad stay overall. Nice location opposite the police headquarters and courthouse. Friendly staff. Brianna the hostess was very nice. The suite was very large. The only thing is that the carpet needs changing. The continental breakfast wasn't appetizing but there's food all around the area. But all in all it was an enjoyable stay."
The price is CA $208
CA $239 total
includes taxes & fees
Jun 10 - Jun 11
Stamford Suites
Pool
Business or Weekend escape
9.8 out of 10, Exceptional, (11)
"The place was clean. Very comfortable. He had refreshments in the fridge. 2nd time here. The host is very easy to get to answer from. We are coming back again soon."
The price is CA $109
CA $192 total
includes taxes & fees
May 28 - May 29
Business or Weekend escape
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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 CA $281
CA $399 total
includes taxes & fees
May 28 - May 29
DUNE Fairfield Beach
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
On the beach, sun loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (58)
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Beach nearby, beach towels
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, (75)
"We had such an awesome stay! Check in process was easy! Amazing scenery amazing adventure we had with our two furr babies!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
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
Terrace/patio
Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (9)
"Beautiful spacious apartment with everything you would need for a comfortable stay. Quick responses to our questions by owners. An easy and convenient location just a short drive to visit our daughter at nearby University. Highly recommend this apartment. "
The price is CA $189
CA $560 total
includes taxes & fees
May 28 - May 29
Luxury Designer 2 bedroom+office/3bed vacation home.
Beach nearby, beach towels
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (15)
"Donna, the host, was absolutely wonderful. Very responsive. Cute beach bungalow. Very comfortable. Perfect for the three of us, 2 adults and 19 year old daughter. Would absolutely recommend."
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Outdoor pool, a heated pool
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, (14)
"The guest house was spacious and well appointed. The furnishings were very comfortable. The grounds at the house are beautiful. We thoroughly enjoyed our stay."
The price is CA $764
CA $1,102 total
includes taxes & fees
May 28 - May 29
Westport Paradise With Every Amenity!
Property grounds
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.6 out of 10, Exceptional, (20)
"We came for a girls weekend. The house is beautiful with plenty of comfy seating. Super clean. The view is beautiful and fun to watch all the boaters. We could not get fire pit to work, but this could have been user error. I would caution others that the stairs are a lot! Definitely not for elders and a real workout, but this was clearly stated in description. Otherwise an absolute dream house with plenty of space. The attention to detail and decor (especially in the bathrooms) was appreciated!...
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
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
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (16)
"We really enjoyed staying at this cottage, much better than 2 rooms in a hotel. Very quiet, fully equipped kitchen.Easy to prepare meals when we wished. We visit the Ridgefield area several times per year and will definitely consider staying here again."
Serenity Awaits at this Cozy Lakeside Bungalow
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
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 CA $200
CA $351 total
includes taxes & fees
Jun 4 - Jun 5
The Safe House - High Tech Apt #2 - 3 Beds
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
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!
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.
Studio Suite, Kitchen | Private kitchen
Guesthouse at Norwalk Inn
3.5 star property
8.4 out of 10, Very good, (37)
"The pictures are very deceiving - as they are of the Guesthouses not the main hotel. I thought I was booking at an Inn, but I was really booked at a regular ole chain hotel. One that charges $8 per person per day for their pool! (you should really change this policy for paying overnight guests - why should we pay additional for facilities like this?) There's also nowhere to walk to from here, so if you're without a car expect to be paying for Ubers everywhere (which is fine as they're readily...
The price is CA $309
CA $356 total
includes taxes & fees
Jun 25 - Jun 26
Guesthouse at Norwalk Inn
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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.

Weston Vacation Rental Travel Info

Other types of properties in Weston you may be interested in

Front of property
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very good, (1507)
"Great older hotel at very reasonable price for the area."
The price is CA $137
CA $158 total
includes taxes & fees
May 28 - May 29
Amsterdam Hotel
Individually decorated, individually furnished, desk, laptop workspace
EVEN Hotel Norwalk, an IHG Hotel
3.5 star property
8.2 out of 10, Very good, (1004)
"Was just an overnight stay sucks they don’t offer free breakfast with booking but the place overall was great and the hotel room was cute and clean. Would definitely stay again!!"
The price is CA $185
CA $212 total
includes taxes & fees
May 30 - May 31
EVEN Hotel Norwalk, an IHG Hotel
Premium bedding, desk, laptop workspace, iron/ironing board
The Circle Hotel Fairfield
3.0 star property
8.8 out of 10, Excellent, (1105)
"Very comfortable accommodations. I would definitely recommend this hotel."
The price is CA $183
CA $211 total
includes taxes & fees
May 29 - May 30
The Circle Hotel Fairfield
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Weston. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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