A calm lake surrounded by dense forest and a cloudy sky.

Weston Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Weston vacation rentals

A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

1. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is P22,532
P25,912 total
includes taxes & fees
Oct 11 - Oct 12
Guesthouse at Norwalk Inn
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (114 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is P11,159
P16,669 total
includes taxes & fees
Oct 12 - Oct 13
DUNE Fairfield Beach
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

3. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (189 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is P9,509
P10,936 total
includes taxes & fees
Oct 15 - Oct 16
Stamford Suites
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

4. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is P38,223
P58,083 total
includes taxes & fees
Oct 22 - Oct 23
4 Mi to Beach & Dtwn! Charming Fairfield Home
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

5. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is P65,466
P97,298 total
includes taxes & fees
Oct 11 - Oct 12
Beechmont - Perfect for Family Retreat!
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

6. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is P20,649
P31,693 total
includes taxes & fees
Oct 11 - Oct 12
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Weston Hotel Reviews

J House Greenwich

J House Greenwich

10/10 Excellent
"Rooms were clean, check- in was easy Staff was excellent , breakfast was great Tony’s restaurant was over the top so was Tony!! Over all great experience Would definitely stay again"
Sarah 1-night trip
Posted 1 hour ago
J House Greenwich

Find out more about Weston

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.

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 Stepping Stones Museum for Children, 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.