Weston Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Weston

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (33)
"This cottage is so beautiful, well equipped and comfortable. The hosts were welcoming, accommodating and checked in with us to make certain we were enjoying our visit. The gorgeous location was perfect for us. We were visiting family in the area which is why we chose it. We didn’t realize how near it was to quaint towns, great restaurants, etc. We also spent an afternoon at nearby Sherwood Island followed by lobster rolls at a nearby restaurant. Thank you! Looking forward to a return visit! "
The price is AU$466
includes taxes & fees
1 Dec - 2 Dec
Adorable 1-Bedroom Cottage in Weston, CT

Stamford Suites

2.5 star property
6.8 out of 10, (766)
"All is well"
The price is AU$374
includes taxes & fees
6 Dec - 7 Dec
Stamford Suites

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AU$154
includes taxes & fees
2 Dec - 3 Dec
Business or Weekend escape

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (42)
"Beautiful and convenient location in a pretty neighborhood. Fairlt quiet on the 3rd floor, although some late night noise from party-ers but that was made clear on the website. Walkable to town and beach. Very comfortable stay! Thank you!"
The price is AU$420
includes taxes & fees
1 Dec - 2 Dec
DUNE Fairfield Beach

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (74)
"The house is as advertised. Good amount of room. The host was pretty communicative. No complaints from the property. Just wish they had a bigger table for group dinners"
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (86)
"Perfectly adorable house that was ideal for our brief getaway. I wish we had been able to use the kayak/canoe but time was tight. The only issue was the driveway which had me holding my breath a bit but luckily we were careful and managed without incident."
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (114)
"Enjoyed the theater room and the comfortable bed"
Lower Lvl Private 2BR/1BA Family/Pet Friendly

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

9.4 out of 10, Exceptional, (15)
"Great little spot. Central enough to get everywhere we needed to. Walked to restaurants and to a concert (about 30 minutes). Host had some treats for us when we checked in. Apartment was clean and spacious. Felt comfortable walking around the neighborhood "
The price is AU$656
includes taxes & fees
1 Dec - 2 Dec
Luxury Designer 2 bedroom+office/3bed vacation home.

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (25)
"The house was clean, and very comfortable. They are well stocked, even with our odd allergies, we were able to find some snacks. It saved us a good amount of town since it was a short visit. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Westport Paradise With Every Amenity!

10.0 out of 10, Exceptional, (23)
"We had such a nice stay at Mark and Sarah’s. Check in was so easy and they were very attentive to anything we needed. The property and apartment are beautiful, it was so nice waking up and seeing all the trees and it was so quiet. We will definitely be back and stay when we are visiting our daughter at Fairfield."
The price is AU$1,099
includes taxes & fees
1 Dec - 2 Dec
Westport Paradise With Every Amenity!

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (26)
"The view in the fall was amazing! So relaxing to sit and watch the lake while having our coffee. The owners are amazing. Everything we needed and more. Plenty of room for the family or even if multiple families stayed. Would stay here again!"
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

8.6 out of 10, Excellent, (4)
"The location of Ms. Jay's place is unbeatable! My group and I were in town for an event in the Total Mortgage Arena. The drive was 5 minutes max! Ms. Jay is great with communication. She was always available for any questions. The apartment is very homey, cozy and comfortable. Very nicely decorated and it has everything you might need. (We would just recommend some mirrors in the bedrooms). The place is next to a very busy street which there is always a lot of noise, especially at night. One...
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"Great space would be better if there were kuerig cups to go with the machine in the kitchen"
The price is AU$493
includes taxes & fees
1 Dec - 2 Dec
Guesthouse at Norwalk Inn

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (23)
"Washer downstairs unavailable, thermostat only on request, feather pillows (allergy). Otherwise it was ok with plenty of bedrooms and baths. "
Cheerful 4 bedrooms residential house.

Beachfront 3-bedroom vacation home just 14 minutes from Yale University

10.0 out of 10, Exceptional, (28)
"Very comfortable home. Perfect for our grown family. We enjoyed the relaxed atmosphere, the beach and water views right outside the back steps. We set up our umbrellas and chairs, had fun using the kyack and paddle board. It was a wonderful and relaxing time together! Looking forward to it again next year."
Beachfront 3-bedroom vacation home just 14 minutes from Yale University

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

10.0 out of 10, Exceptional, (78)
"Very large house just like the photos. Host is present and responsive. We had the entire property to ourselves. Nice yard for some whiffle ball and outdoor activities. Swimming is possible at the public lake access which is about a mile away or so. Overall, a very nice stay at a very nice property. We were 10 adults (friends weekend) and fit just fine. "
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

The Safe House - High Tech Apt #3 - 4 beds

9.8 out of 10, Exceptional, (38)
"We had a great stay at the apt. Very clean and well kept. It is in a great location close to everything. Very responsive manager, Rob. Enjoyed it! Thx. "
The price is AU$376
includes taxes & fees
16 Dec - 17 Dec
The Safe House - High Tech Apt #3 - 4 beds

The Safe House - High Tech Apt #2 - 3 Beds

9.6 out of 10, Exceptional, (35)
"Enjoyed my second stay at the Safe House. Plenty of space, great proximity to Greenwich downtown."
The price is AU$321
includes taxes & fees
3 Dec - 4 Dec
The Safe House - High Tech Apt #2 - 3 Beds

Studio OSM · Sunny Westport Studio Apt. Above Historic Mill

10.0 out of 10, Exceptional, (67)
"Can’t say enough good things about studio apartment! Gerard was wonderful and easy to communicate with. This apartment had absolutely everything we needed! The airline lost one of our bags, so the onsite washing machine was very much appreciated! We will definitely be back to stay here again!"
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill
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.
Don't see what you're looking for?
See all available properties in Weston
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Weston you may be interested in

Amsterdam Hotel

2.0 star property
8.4 out of 10, Very good, (1723)
"My room was neat and clean, everything was working and tge staff was nice"
The price is AU$178
includes taxes & fees
1 Dec - 2 Dec
Amsterdam Hotel

The Circle Hotel Fairfield

3.0 star property
8.8 out of 10, Excellent, (1333)
"Love this hotel"
The price is AU$218
includes taxes & fees
1 Dec - 2 Dec
The Circle Hotel Fairfield

Trumbull Marriott Shelton

3.5 star property
8.4 out of 10, Very good, (1073)
"N/A"
The price is AU$224
includes taxes & fees
8 Dec - 9 Dec
Trumbull Marriott Shelton
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Business or Weekend escape: This holiday home rental outside of Weston is equipped with a BBQ, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

How many holiday rentals are there in Weston?

Choose from 14 Expedia holiday rentals in Weston for a memorable holiday.

What’s there to see and do in Weston?

Lucius Pond Ordway / Devil's Den Preserve and Trout Brook Valley State Park Reserve are a couple of lovely local spots to get outside and enjoy nature. Westport Country Playhouse and Westport Farmers Market 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.