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

Weston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
$327 nightly
The price is $376
Oct 18 - Oct 19
Total with taxes and fees
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, (115 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$235 nightly
The price is $270
Oct 29 - Oct 30
Total with taxes and fees
DUNE Fairfield Beach
A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a large plant.

3. Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
$253 nightly
The price is $275
Oct 20 - Oct 21
Total with taxes and fees
Spacious Studio with Pool Table
A room with a dark wooden door, white paneled walls, a woven mirror, a wicker basket, a cushioned chair, and a small round table.

4. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.4 out of 10, Exceptional, (18 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
$473 nightly
The price is $536
Oct 22 - Oct 23
Total with taxes and fees
Nama-stay, sweet pink Saugatuck Shores beach cottage
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

5. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (194 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$164 nightly
The price is $189
Oct 18 - Oct 19
Total with taxes and fees
Stamford Suites
A room with a wooden floor, a black leather chair, a piano, and a large window with a view of a deck and trees.

6. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
9.8 out of 10, Exceptional, (11 reviews)
"lovely porch and backyard."
United States
Kaia W.
$914 nightly
The price is $1,038
Nov 14 - Nov 15
Total with taxes and fees
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
A two-story house with a front porch, a chimney, and a well-maintained garden with a stone pathway leading to the entrance.

7. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
$498 nightly
The price is $567
Oct 18 - Oct 19
Total with taxes and fees
Gilded Age Luxury Surrounded by Nature
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

8. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
$501 nightly
The price is $568
Oct 21 - Oct 22
Total with taxes and fees
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

9. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (15 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
$583 nightly
The price is $661
Nov 9 - Nov 10
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A corner seating area with two chairs and a table, a patterned rug, and a wooden railing.

10. King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
$315 nightly
The price is $357
Oct 19 - Oct 20
Total with taxes and fees
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

11. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (19 reviews)
"Place was very clean . Communication between owner and us was excellent."
United States
gail s.
$546 nightly
The price is $619
Nov 16 - Nov 17
Total with taxes and fees
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A beige sofa with blue cushions, a white vase with flowers, and a white door with a glass panel.

12. Modern Apartment with Private Entrance

Modern Apartment with Private Entrance
Historic District
10.0 out of 10, Exceptional, (1 review)
"This was a great deal on the busy weekend we stayed. The space was even better than described."
United States
Derek H.
$261 nightly
The price is $297
Oct 20 - Oct 21
Total with taxes and fees
Modern Apartment with Private Entrance
A white room with a round table, two benches, and a window with a view of houses.

13. Stay at Black Rock Harbor

Stay at Black Rock Harbor
Black Rock Historic District
10.0 out of 10, Exceptional, (29 reviews)
"This house was perfect for our family. Will definitely use again when we're visiting family in the area."
United States
Laura L.
$803 nightly
The price is $911
Nov 1 - Nov 2
Total with taxes and fees
Stay at Black Rock Harbor
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

14. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.4 out of 10, Exceptional, (20 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
$690 nightly
The price is $782
Oct 20 - Oct 21
Total with taxes and fees
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

15. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
$805 nightly
The price is $925
Oct 18 - Oct 19
Total with taxes and fees
4 Mi to Beach & Dtwn! Charming Fairfield Home
A bedroom with a bed, a TV, a ceiling fan, a window with stained glass, and several potted plants.

16. 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
9.4 out of 10, Exceptional, (18 reviews)
"The accommodations were incredible. The host provided many helpful materials that made the stay very comfortable. The apartment was very cute and had nice amenities for the guests that go above any beyond what a hotel can provide."
United States
Bailey
$205 nightly
The price is $232
Oct 18 - Oct 19
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A modern living room with a sofa, coffee table, and a bed in the background.

17. Renovated 3BR Apt / Easy Check-In / FamilyFriendly

Renovated 3BR Apt / Easy Check-In / FamilyFriendly
West End - West Side
10.0 out of 10, Exceptional, (1 review)
"Unit was clean, beds were large and comfy. Very close to downtown. Would stay again!"
United States
Matthew
$307 nightly
The price is $348
Nov 2 - Nov 3
Total with taxes and fees
Renovated 3BR Apt / Easy Check-In / FamilyFriendly
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

18. Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
$211 nightly
The price is $239
Oct 18 - Oct 19
Total with taxes and fees
Centric property close to all the great things in the city
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

19. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
10.0 out of 10, Exceptional, (1 review)
"Beautiful home! Host was super responsive to questions. The entire house was super clean and welcoming. The bed was comfortable and smelled fresh. There was a personalized welcome sign that was a nice touch and some (much needed) snacks after our almost 3 hour drive. Expectations were well within reason and easily manageable. I would 100% rent again."
United States
Raelyn O.
$815 nightly
The price is $923
Oct 18 - Oct 19
Total with taxes and fees
4 Mi to Beach & Dtwn! Charming Fairfield Home
A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with a kettle, and a painting on the wall.

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

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
9.6 out of 10, Exceptional, (4 reviews)
"Nice place to stay "
United States
Maria Elena G.
$356 nightly
The price is $403
Nov 3 - Nov 4
Total with taxes and fees
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
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

Amsterdam Hotel

Amsterdam Hotel

8/10 Good
"Good hotel"
John 1-night trip
Posted less than an hour ago
Amsterdam Hotel

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 $152 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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental outside of Weston offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.