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

Weston Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Weston holiday rentals

A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

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 AU$377
includes taxes & fees
5 Oct - 6 Oct
DUNE Fairfield Beach
A modern living room with a flat-screen TV mounted on the wall, a round coffee table, and a sofa.

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 AU$360
includes taxes & fees
29 Sept - 30 Sept
Spacious Studio with Pool Table
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

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 AU$459
includes taxes & fees
8 Oct - 9 Oct
Guesthouse at Norwalk Inn
A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

4. 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 AU$332
includes taxes & fees
29 Sept - 30 Sept
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

5. 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 AU$554
includes taxes & fees
29 Sept - 30 Sept
Luxury Designer 2 bedroom+office/3bed vacation home.
A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

6. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is AU$610
includes taxes & fees
29 Sept - 30 Sept
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.

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 AU$809
includes taxes & fees
30 Sept - 1 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

8. 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 AU$471
includes taxes & fees
29 Sept - 30 Sept
Modern 2 Bed in BlackRock
A modern kitchen with white cabinetry, a granite countertop, and a built-in island with bar stools.

9. 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 AU$424
includes taxes & fees
29 Sept - 30 Sept
Zen, Spacious & Comfy 2 bed, Lux beds
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

10. 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 AU$379
includes taxes & fees
4 Oct - 5 Oct
Centric property close to all the great things in the city
A covered outdoor seating area with wicker sofas, a fire pit, and string lights.

11. 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.
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

12. 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 AU$985
includes taxes & fees
19 Oct - 20 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A modern living room with a large window, a sofa, a coffee table, and a TV.

13. Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
9.6 out of 10, Exceptional, (13 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is AU$277
includes taxes & fees
27 Oct - 28 Oct
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
A modern living room with a sofa, coffee table, and a bed in the background.

14. 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
The price is AU$547
includes taxes & fees
6 Oct - 7 Oct
Renovated 3BR Apt / Easy Check-In / FamilyFriendly
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

15. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (185 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is AU$253
includes taxes & fees
30 Sept - 1 Oct
Stamford Suites
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

16. 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 AU$816
includes taxes & fees
30 Sept - 1 Oct
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

17. Elite room stay

Elite room stay
Bridgeport
The price is AU$487
includes taxes & fees
29 Sept - 30 Sept
Elite room stay
A swimming pool at night with blue lighting.

18. 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 AU$220
includes taxes & fees
4 Oct - 5 Oct
Business or Weekend escape
A room with a large arched window, a bed, a bedside table, a lamp, and a potted plant.

19. Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (8 reviews)
"The Orange & Groovy Apt. was as described. All the amenities we needed and we had a lovely time and enjoyed the area. Will book again!"
United States
Betty W.
The price is AU$335
includes taxes & fees
29 Sept - 30 Sept
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
A neatly arranged bedroom with a bed, bedside table, bench, and wall decor.

20. 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
9.0 out of 10, Wonderful, (2 reviews)
"It was clean "
United States
Burton
The price is AU$454
includes taxes & fees
6 Oct - 7 Oct
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

8/10 Good
"The hotel was very clean and spacious. Even though there were several large events going on while we were there, there was ample parking, space to relax and no lack in service. It never felt crowded or excessively noisy. We did not use the gym but it was very well organized and clean with working equipment. We did use the pool every day. I do think for the price there should have been a complimentary breakfast and coffee bar. They could have offered a discount at the small coffee shop in the lobby. Unfortunately when our son and his children arrived the room they were given was completely unmade. They had to be relocated to another room. I would recommend this hotel to others."
Marc 4-night trip
Posted 3 hours ago
Hyatt Regency Greenwich

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, 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 favourite 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 depend 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 AU$220 per night. Entering your travel dates in the search wizard might find you 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?

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.