Weston Vacation Rentals

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, (26)
"The cottage has everything you need! Everything- very clean and cute! This owner is great and our family and dog love it!"
The price is $195
$303 total
includes taxes & fees
Jun 14 - Jun 15
Adorable 1-Bedroom Cottage in Weston, CT
Stamford Suites
Exterior
Stamford Suites
2.5 star property
6.8 out of 10, (719)
"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 $169
$195 total
includes taxes & fees
Jun 12 - Jun 13
Stamford Suites
Business or Weekend escape
Pool
Business or Weekend escape
9.6 out of 10, Exceptional, (12)
"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 $75
$135 total
includes taxes & fees
Jun 12 - Jun 13
Business or Weekend escape
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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 $204
$290 total
includes taxes & fees
Jun 6 - Jun 7
DUNE Fairfield Beach
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
On the beach, sun loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (59)
"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
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
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
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (104)
"Neighborhood great for walking dogs. Would have loved a sink besides bathroom. Overall great value."
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Luxury Designer 2 bedroom+office/3bed vacation home.
Terrace/patio
Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (10)
"Had a great stay!"
The price is $128
$397 total
includes taxes & fees
Jun 24 - Jun 25
Luxury Designer 2 bedroom+office/3bed vacation home.
Westport Paradise With Every Amenity!
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 $585
$841 total
includes taxes & fees
Jun 7 - Jun 8
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, (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
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Property grounds
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.8 out of 10, Exceptional, (21)
"The property was as described and the living space was perfect for our visit. The deck and views are amazing. If staying at this property, you just need to be aware that it is very difficult getting luggage and groceries into the property. You have to go down a long flight of stairs, walk down a very steep driveway and then go down another flight of stairs. Once you are in, bedroom access requires that you go up or down additional stairs."
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Serenity Awaits at this Cozy Lakeside Bungalow
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (18)
"Stayed while attending a local wedding and wished we had had more time to hang out at the house! The lake is beautiful and the house had everything we needed! Hope to come back some day!"
Serenity Awaits at this Cozy Lakeside Bungalow
(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, (2)
"Amazing place to stay people are great"
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
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 Safe House - High Tech Apt #2 - 3 Beds
Guesthouse at Norwalk Inn
Studio Suite, Kitchen | Private kitchen | Mini-fridge, coffee/tea maker
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 $210
$242 total
includes taxes & fees
Jun 6 - Jun 7
Guesthouse at Norwalk Inn
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
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
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, (72)
"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!
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
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.
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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

Number of vacation rentals
16
Popular accommodation
Weston private vacation homes
Known landmarks
Norwalk Maritime Aquarium, Ridgefield Playhouse and Jennings Beach
International airports
New York, NY (JFK-John F. Kennedy Intl.), Newark, NJ (EWR-Liberty Intl.) and New York, NY (LGA-LaGuardia)

Other types of properties in Weston you may be interested in

Amsterdam Hotel
Front of property
Amsterdam Hotel
2.0 star property
8.4 out of 10, Very Good, (1520)
"Good value. Very clean. Very nice staff. The room is outdated. Beds were too soft not too comfortable. AC worked well but was loud when it kicked on. I would definitely recommend this property if you need a clean , friendly place to stay for a good price."
The price is $90
$105 total
includes taxes & fees
Jun 18 - Jun 19
Amsterdam Hotel
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, (1127)
"Great property & great pool. Just a few signs of wear otherwise great property & great free breakfast! Walking to things nearby isn’t incredibly walk friendly despite being close due to lack of sidewalks & fast traffic. Otherwise great location. "
The price is $129
$148 total
includes taxes & fees
Jun 30 - Jul 1
The Circle Hotel Fairfield
La Quinta Inn & Suites by Wyndham Stamford / New York City
A heated pool
La Quinta Inn & Suites by Wyndham Stamford / New York City
2.5 star property
5.6 out of 10, (1090)
"Nice. Reliable. Clean. Hospitality. Good"
The price is $79
$91 total
includes taxes & fees
Jun 16 - Jun 17
La Quinta Inn & Suites by Wyndham Stamford / New York City
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.

Everything you need to know about Weston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Weston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Weston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Weston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Weston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Weston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Weston rentals

At Expedia, we put the best Weston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Weston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Weston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Weston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

5/5 Excellent
"Nice people."
A verified traveler stayed at Hyatt Regency Greenwich
Posted 1 day ago
Hyatt Regency Greenwich