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

Weston Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Weston holiday rentals

1. Dream Vacation Home

Dream Vacation Home
Derby
The price is NZ$443
includes taxes & fees
4 Aug - 5 Aug
Dream Vacation Home

2. Modern Apartment with Private Entrance

Modern Apartment with Private Entrance
Historic District
The price is NZ$455
includes taxes & fees
18 Aug - 19 Aug
Modern Apartment with Private Entrance

3. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is NZ$725
includes taxes & fees
1 Sept - 2 Sept
Gilded Age Luxury Surrounded by Nature

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

4 BR VILLA, celebration welcome, No Cleaning fee
West Norwalk
The price is NZ$958
includes taxes & fees
16 Aug - 17 Aug
4 BR VILLA, celebration welcome, No Cleaning fee

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

Avora | Quiet Luxury | Downtown Stamford | 2BR/2BA
Downtown Stamford
The price is NZ$991
includes taxes & fees
16 Aug - 17 Aug
Avora | Quiet Luxury | Downtown Stamford | 2BR/2BA

6. 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.
The price is NZ$503
includes taxes & fees
26 Aug - 27 Aug
Sumak Kawsay - Life in harmony. Waterfront Hot Tub + NYC

7. 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
The price is NZ$454
includes taxes & fees
24 Aug - 25 Aug
DUNE Fairfield Beach

8. 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$702
includes taxes & fees
4 Aug - 5 Aug
Guesthouse at Norwalk Inn

9. 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.
The price is NZ$1,516
includes taxes & fees
27 Aug - 28 Aug
Spacious Family Home

10. 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, (6 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.
The price is NZ$1,351
includes taxes & fees
2 Sept - 3 Sept
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

11. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NZ$1,819
includes taxes & fees
4 Aug - 5 Aug
Beechmont - Perfect for Family Retreat!

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)
"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.
The price is NZ$1,184
includes taxes & fees
4 Aug - 5 Aug
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

13. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (149 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is NZ$275
includes taxes & fees
10 Aug - 11 Aug
Stamford Suites

14. 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, (13 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
The price is NZ$393
includes taxes & fees
4 Aug - 5 Aug
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

15. 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$504
includes taxes & fees
24 Aug - 25 Aug
Spacious Studio with Pool Table

16. 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.
The price is NZ$717
includes taxes & fees
23 Aug - 24 Aug
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

17. 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.
The price is NZ$2,145
includes taxes & fees
4 Aug - 5 Aug
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

18. 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.
The price is NZ$1,129
includes taxes & fees
1 Sept - 2 Sept
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

19. 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.
The price is NZ$1,315
includes taxes & fees
4 Aug - 5 Aug
Spacious Retreat with Game Room and Fire Pit

20. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is NZ$386
includes taxes & fees
11 Aug - 12 Aug
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Weston Hotel Reviews

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 favorite 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 depends 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 NZ$249 per night. Entering your travel dates in the search wizard you might find 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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of Weston is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

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.