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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Weston vacation rentals

3 bedrooms, iron/ironing board, WiFi (free)

1. Dream Vacation Home

Dream Vacation Home
Derby
$240 nightly
The price is $272
Sep 6 - Sep 7
Total with taxes and fees
Dream Vacation Home
Dining

2. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
$397 nightly
The price is $450
Sep 2 - Sep 3
Total with taxes and fees
Gilded Age Luxury Surrounded by Nature
Private kitchen

3. 4 BR VILLA, celebration welcome, No Cleaning fee

4 BR VILLA, celebration welcome, No Cleaning fee
West Norwalk
$511 nightly
The price is $579
Aug 16 - Aug 17
Total with taxes and fees
4 BR VILLA, celebration welcome, No Cleaning fee
TV, stereo

4. Avora | Quiet Luxury | Downtown Stamford | 2BR/2BA

Avora | Quiet Luxury | Downtown Stamford | 2BR/2BA
Downtown Stamford
$597 nightly
The price is $597
Aug 15 - Aug 16
Total with taxes and fees
Avora | Quiet Luxury | Downtown Stamford | 2BR/2BA
Exterior

5. Sumak Kawsay - Life in harmony. Waterfront Hot Tub + NYC

Sumak Kawsay - Life in harmony. Waterfront Hot Tub + NYC
Newtown
10.0 out of 10, Exceptional, (1 review)
"What a beautiful, cozy and super well kept place. We absolutely enjoyed our stay and the place had everything we needed. My favorite part was sitting on the back deck watching the boats go by. So peaceful. The place is super close to a cute town which we didn’t have time to explore but we will be back!"
United States
Linsey B.
$257 nightly
The price is $292
Aug 13 - Aug 14
Total with taxes and fees
Sumak Kawsay - Life in harmony. Waterfront Hot Tub + NYC
Classic Suite | Iron/ironing board, WiFi (free), bed sheets

6. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (103 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
$264 nightly
The price is $304
Aug 24 - Aug 25
Total with taxes and fees
DUNE Fairfield Beach
Standard Room, 1 King Bed, Main Building | Property entrance

7. 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
$359 nightly
The price is $413
Aug 9 - Aug 10
Total with taxes and fees
Guesthouse at Norwalk Inn
Private kitchen

8. Spacious Family Home

Spacious Family Home
Westport
10.0 out of 10, Exceptional, (1 review)
"We had a getaway weekend for a close friend group from college. This location could not have been better! We had everything we needed. Four bedrooms and three full bathrooms and across the street, a bakery, pizza place, fantastically stocked market, and a nice restaurant! A short drive allowed us to enjoy shopping and more food choices, as well as giving our Manhattan friend easy access to the train. Really could not have been a better place for us. Communication with the host was timely,...
United States
Laura B.
$792 nightly
The price is $897
Aug 25 - Aug 26
Total with taxes and fees
Spacious Family Home
Smart TV

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

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
$676 nightly
The price is $766
Aug 25 - Aug 26
Total with taxes and fees
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Front of property

10. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
$924 nightly
The price is $1,062
Aug 19 - Aug 20
Total with taxes and fees
Beechmont - Perfect for Family Retreat!
Smart TV, fireplace, books, stereo

11. 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)
"This house was so lovely, clean, cozy, and well-appointed - everything we could have asked for for a girls' weekend! And so close to the town of Westport with its excellent restaurants and shops. The best!"
United States
Rebecca H.
$671 nightly
The price is $760
Aug 9 - Aug 10
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Exterior

12. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (152 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
$134 nightly
The price is $155
Aug 9 - Aug 10
Total with taxes and fees
Stamford Suites
1 bedroom, desk, iron/ironing board, WiFi (free)

13. 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
9.8 out of 10, Exceptional, (14 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
$203 nightly
The price is $230
Aug 9 - Aug 10
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
1 bedroom, desk, WiFi, bed sheets

14. 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
$291 nightly
The price is $318
Sep 1 - Sep 2
Total with taxes and fees
Spacious Studio with Pool Table
Dining

15. 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.
$371 nightly
The price is $420
Aug 23 - Aug 24
Total with taxes and fees
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Exterior

16. Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
8.8 out of 10, Excellent, (10 reviews)
"Plenty of bedrooms and space for the family. Very prompt communication with host."
United States
David K.
$1,097 nightly
The price is $1,245
Aug 11 - Aug 12
Total with taxes and fees
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
Beach nearby, sun loungers, beach towels

17. 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, (38 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
$598 nightly
The price is $677
Sep 1 - Sep 2
Total with taxes and fees
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Coffee/tea maker, fridge, microwave, oven

18. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, Exceptional, (2 reviews)
"A great location. We were less than 15 minutes from everything we did. House was a super layout for our large group."
United States
Mark F.
$746 nightly
The price is $844
Aug 27 - Aug 28
Total with taxes and fees
Spacious Retreat with Game Room and Fire Pit
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

19. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
$205 nightly
The price is $232
Aug 11 - Aug 12
Total with taxes and fees
2-bedroom apartmet No cleaning Fee
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 Watershed

The Watershed

10/10 Excellent
"Fantastic property to stay at. The hotel is beautiful and well kept. I would highly recommend."
Katie 1-night trip
Posted less than an hour ago
The Watershed

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 $147 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?

Charming Home in Seaside: This vacation home rental outside of Weston is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.