Weston Vacation Rentals

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Our top choices for Weston vacation rentals

Exclusive Apartment | Private kitchen | Mini-fridge, microwave, oven, stovetop
The Mansion Hotel-style

Aparthotel in Norwalk

2.5 star property
8.6 out of 10, Excellent, (19)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
$88 nightly
The price is $102
Dec 11 - Dec 12
Total with taxes and fees
The Mansion Hotel-style
1 bedroom, desk, iron/ironing board, free WiFi
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Apartment in Downtown Bridgeport

10.0 out of 10, Exceptional, (2)
"Ricardo’s place was perfect for our needs! A small, clean and cozy place, not far from our daytime destination, the apartment offers all the basics - kitchenette, nice bathroom and modern shower, a comfy Queen Size bed, and even some snacks and essentials for a comfortable stay. The area has some restraunts and bars nearby too, though we were happy to stay in and watch some Netflix. I would highly recommend this apartment to a friend, and Ricardo has been a pleasure. Thanks so much!"
United States
Anonymous traveler
$145 nightly
The price is $164
Dec 11 - Dec 12
Total with taxes and fees
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
2 bedrooms, iron/ironing board, travel crib, WiFi
Renovated 2BR Retreat / Modern Comforts Included

Apartment in West End - West Side

10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
$255 nightly
The price is $289
Dec 11 - Dec 12
Total with taxes and fees
Renovated 2BR Retreat / Modern Comforts Included
Pool
Business or Weekend escape

Vacation Home in Stratford

9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
$130 nightly
The price is $147
Jan 1 - Jan 2, 2026
Total with taxes and fees
Business or Weekend escape
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Vacation Home in Shelton

9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
$174 nightly
The price is $197
Dec 11 - Dec 12
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Interior
Private Apartment in Southbury 101

Apartment in Southbury

9.4 out of 10, Exceptional, (6)
"Great stay. Clean, open space, easy access, and a nice pond in back to bring the dog. Would come back again."
United States
Rooster D.
$263 nightly
The price is $298
Dec 16 - Dec 17
Total with taxes and fees
Private Apartment in Southbury 101
Exterior
New One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$110 nightly
The price is $124
Dec 11 - Dec 12
Total with taxes and fees
New One Bedroom Apartment Centrally Located in Southbury
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

Apartment in Fairfield

3.0 star property
9.0 out of 10, Wonderful, (77)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
$232 nightly
The price is $267
Dec 11 - Dec 12
Total with taxes and fees
DUNE Fairfield Beach
Fridge, microwave, oven, stovetop
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Apartment in Fairfield

10.0 out of 10, Exceptional, (1)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
$279 nightly
The price is $316
Dec 11 - Dec 12
Total with taxes and fees
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Fridge, microwave, oven, stovetop
Private Apartment in Southbury 103

Apartment in Southbury

10.0 out of 10, Exceptional, (2)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
$246 nightly
The price is $279
Dec 14 - Dec 15
Total with taxes and fees
Private Apartment in Southbury 103
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Vacation Home in Greenwich

9.6 out of 10, Exceptional, (23)
"The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. "
United States
Victoria R.
$228 nightly
The price is $258
Dec 15 - Dec 16
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Fridge, microwave, oven, stovetop
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

Apartment in Brooklawn - St. Vincent

8.0 out of 10, Very Good, (1)
"It was clean "
United States
Burton
$255 nightly
The price is $289
Dec 11 - Dec 12
Total with taxes and fees
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Dining tables
The ARLO - Walk to Brewery and Restaurants

Vacation Home in Milford

9.4 out of 10, Exceptional, (3)
"Very nice house....loved the front enclosed porch, and the kitchen was amazing with everything we needed. The deck with the Blackstone Grill was a great place to sit and relax. We enjoyed many of the nearby restaurants too. Matt and Jess were great hosts!J&J, Mooresville, NC"
United States
Jena
$322 nightly
The price is $365
Dec 11 - Dec 12
Total with taxes and fees
The ARLO - Walk to Brewery and Restaurants
Property grounds
#37 - Luxury Collection

Vacation Home in Stratford

2.0 star property
8.0 out of 10, Very Good, (4)
"We enjoyed the coziest getaway at this property. Newly renovated, clean and tucked away without being accessible to local attractions. "
United States
Sarah T.
$359 nightly
The price is $381
Dec 15 - Dec 16
Total with taxes and fees
#37 - Luxury Collection
Apartment (1 Bedroom) | Interior
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Apartment in Greenwich

3.0 star property
$201 nightly
The price is $231
Dec 22 - Dec 23
Total with taxes and fees
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Game room
Peaceful apartment on 3.5 acres w/ artist studio.

Apartment in Brookfield

9.6 out of 10, Exceptional, (20)
"This was a nice get away for us that was not too far away from home."
United States
Isabella M.
$171 nightly
The price is $194
Dec 11 - Dec 12
Total with taxes and fees
Peaceful apartment on 3.5 acres w/ artist studio.
TV, fireplace, books
The Little Lake Cabin with hot tub

Cabin in New Fairfield

10.0 out of 10, Exceptional, (1)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The Little Lake Cabin with hot tub
Fridge, microwave, oven, stovetop
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Vacation Home in Shelton

2.0 star property
$340 nightly
The price is $385
Jan 7 - Jan 8, 2026
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Fridge, microwave, oven, stovetop
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Apartment in West End - West Side

10.0 out of 10, Exceptional, (2)
"Wonderful "
United States
Nolufefe Z.
$349 nightly
The price is $396
Jan 6 - Jan 7, 2026
Total with taxes and fees
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
Interior
Spacious Studio with Pool Table

Apartment in Westport

8.6 out of 10, Excellent, (7)
"So cute and comfortable "
United States
Maria
$245 nightly
The price is $278
Dec 11 - Dec 12
Total with taxes and fees
Spacious Studio with Pool Table
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.
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Top Weston Hotel Reviews

The Circle Hotel Fairfield

The Circle Hotel Fairfield

10/10 Excellent
"Good location close to Fairfield U"
Michelle 1-night trip
Posted 2 days ago
The Circle Hotel Fairfield

Find out more about Weston

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 $138 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.

Explore a world of travel with Expedia

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?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.: This vacation home rental outside of Weston is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

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?

While exploring the area, visit family-friendly sights like Norwalk Maritime Aquarium, or get outside and enjoy nature at Lucius Pond Ordway / Devil's Den Preserve. Trout Brook Valley State Park Reserve and Wilton Historical Society 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.