Holiday Rentals in Weston

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Our top choices for Weston holiday rentals

The Mansion Hotel-style

The Mansion Hotel-style
2.5 star property
West Norwalk
8.2 out of 10, Very good, (22)
"Great service and very clean 👌 "
United States
JEAN
The price is €83
includes taxes & fees
27 Dec - 28 Dec
The Mansion Hotel-style

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
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
The price is €244
includes taxes & fees
4 Jan - 5 Jan 2026
Renovated 2BR Retreat / Modern Comforts Included

New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury
Southbury
9.8 out of 10, Exceptional, (20)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is €109
includes taxes & fees
4 Jan - 5 Jan 2026
New One Bedroom Apartment Centrally Located in Southbury

2 Mi to Beach, Shared Yard Space: West Haven Apt!

2 Mi to Beach, Shared Yard Space: West Haven Apt!
3.0 star property
West Haven
The price is €306
includes taxes & fees
25 Dec - 26 Dec
2 Mi to Beach, Shared Yard Space: West Haven Apt!

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
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.
The price is €170
includes taxes & fees
25 Dec - 26 Dec
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.6 out of 10, Exceptional, (7)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
United States
Caroline
The price is €202
includes taxes & fees
22 Jan - 23 Jan 2026
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Private Apartment in Southbury 101

Private Apartment in Southbury 101
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.
The price is €234
includes taxes & fees
19 Jan - 20 Jan 2026
Private Apartment in Southbury 101

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
2.0 star property
Southbury
10.0 out of 10, Exceptional, (1)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is €179
includes taxes & fees
21 Jan - 22 Jan 2026
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is €128
includes taxes & fees
17 Jan - 18 Jan 2026
Business or Weekend escape

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very good, (1)
"It was clean "
United States
Burton
The price is €243
includes taxes & fees
4 Jan - 5 Jan 2026
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
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.
The price is €277
includes taxes & fees
4 Jan - 5 Jan 2026
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Peaceful apartment on 3.5 acres w/ artist studio.

Peaceful apartment on 3.5 acres w/ artist studio.
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.
Peaceful apartment on 3.5 acres w/ artist studio.

Private Apartment in Southbury 103

Private Apartment in Southbury 103
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.
The price is €230
includes taxes & fees
20 Jan - 21 Jan 2026
Private Apartment in Southbury 103

The ARLO - Walk to Brewery and Restaurants

The ARLO - Walk to Brewery and Restaurants
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
The ARLO - Walk to Brewery and Restaurants

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
10.0 out of 10, Exceptional, (2)
"Wonderful "
United States
Nolufefe Z.
The price is €322
includes taxes & fees
12 Jan - 13 Jan 2026
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.6 out of 10, Exceptional, (4)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
The price is €234
includes taxes & fees
19 Jan - 20 Jan 2026
Private Apartment in Southbury 102

Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford
2.0 star property
Milford
9.0 out of 10, Wonderful, (2)
"Had a great stay!"
United States
Garry G.
The price is €398
includes taxes & fees
23 Jan - 24 Jan 2026
Beach Apartment in Woodmont Milford

Bright Escape, Top-Rated Design, Fire pit, Near Beach

Bright Escape, Top-Rated Design, Fire pit, Near Beach
Fairfield
10.0 out of 10, Exceptional, (11)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
The price is €405
includes taxes & fees
6 Jan - 7 Jan 2026
Bright Escape, Top-Rated Design, Fire pit, Near Beach

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.6 out of 10, Exceptional, (23)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
The price is €231
includes taxes & fees
8 Jan - 9 Jan 2026
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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

Find out more about Weston

Everything you need to know about Weston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Weston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Weston holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Weston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Weston holiday rentals we have selected for you start as low as €108 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Weston rentals

At Expedia, we put the best Weston holiday 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 holiday.

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 holiday rental in Weston?

Yes, there are holiday rentals close to the most popular sights in Weston, or you can select a more secluded option if you're looking for a relaxing stay.

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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.: This holiday 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 holiday rentals are there in Weston?

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

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 wider area.

What’s a holiday rental in Weston like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Weston. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family getaway.