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

Weston Holiday Rentals

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Our top choices for Weston holiday rentals

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is NZ$463
includes taxes & fees
14 Oct - 15 Oct
DUNE Fairfield Beach

2. 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
The price is NZ$441
includes taxes & fees
21 Sept - 22 Sept
Spacious Studio with Pool Table

3. 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 NZ$713
includes taxes & fees
28 Sept - 29 Sept
Guesthouse at Norwalk Inn

4. Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.6 out of 10, Exceptional, (27 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveller
The price is NZ$634
includes taxes & fees
19 Sept - 20 Sept
Luxury Designer 2 bedroom+office/3bed vacation home.

5. 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
The price is NZ$393
includes taxes & fees
19 Oct - 20 Oct
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

6. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is NZ$745
includes taxes & fees
29 Sept - 30 Sept
Gilded Age Luxury Surrounded by Nature

7. 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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is NZ$1,089
includes taxes & fees
20 Sept - 21 Sept
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

8. Elite room stay

Elite room stay
Bridgeport
The price is NZ$592
includes taxes & fees
29 Sept - 30 Sept
Elite room stay

9. 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.
The price is NZ$468
includes taxes & fees
21 Sept - 22 Sept
Centric property close to all the great things in the city

10. 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, (2 reviews)
"Host was attentive and the space was comfortable and exactly what we needed"
United States
Parker M.
The price is NZ$580
includes taxes & fees
22 Sept - 23 Sept
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

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)
"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.
The price is NZ$1,154
includes taxes & fees
19 Oct - 20 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

12. 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.
The price is NZ$1,113
includes taxes & fees
20 Sept - 21 Sept
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

13. Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
7.4 out of 10, Good, (3 reviews)
"Our host forgot we were coming, did not have check-in instructions or access, and did not respond to message or phone call. We had reserved this property to move my daughter across the country and into her dorm in college. Needless to say, an already stressful time was made more stressful as we had to find somewhere new to stay that evening that did not offer the same amenities we had planned on. Very disappointed and made for a rough start to our trip. I was pleased we received a full refund."
United States
Sarah K.
The price is NZ$520
includes taxes & fees
21 Sept - 22 Sept
Zen, Spacious & Comfy 2 bed, Lux beds

14. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (178 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is NZ$320
includes taxes & fees
20 Sept - 21 Sept
Stamford Suites

15. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (5 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
The price is NZ$610
includes taxes & fees
5 Oct - 6 Oct
Modern 2 Bed in BlackRock

16. Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveller
The price is NZ$558
includes taxes & fees
6 Oct - 7 Oct
Renovated 2BR Retreat / Modern Comforts Included

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

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.2 out of 10, Wonderful, (17 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
The price is NZ$1,152
includes taxes & fees
24 Sept - 25 Sept
Nama-stay, sweet pink Saugatuck Shores beach cottage

18. 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 NZ$1,308
includes taxes & fees
28 Sept - 29 Sept
4 Mi to Beach & Dtwn! Charming Fairfield Home

19. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is NZ$252
includes taxes & fees
19 Oct - 20 Oct
Business or Weekend escape

20. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is NZ$593
includes taxes & fees
20 Sept - 21 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Weston holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Weston. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Weston. Seeing all the best attractions is bound to make you fall in love with Weston. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Weston short-term rentals, that won’t be hard to do.

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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Weston offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 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 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.