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Top Holiday Rentals in Weston

Stamford Suites

4.0 star property
5.6 out of 10, (40)
"You walk 2 blocks and bunch of stores and great restaurants. Try Bari restaurant"
Stamford Suites

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (57)
"Simple and efficient check in…clean and rooms!"
DUNE Fairfield Beach

Business or Weekend escape

9.6 out of 10, Exceptional, (38)
"Very nice owner with great communication. "
The price is £110
includes taxes & fees
6 Jul - 7 Jul
Business or Weekend escape

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

9.4 out of 10, Exceptional, (19)
"My stay was good only con was the parking. Parking was in the street and hope you come in early to get a space or you will park down the street… there is parking in the back for a fee which was not in the description of the property upon booking."
The price is £307
includes taxes & fees
1 Jul - 2 Jul
Luxury Designer 2 bedroom+office/3bed vacation home.

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
The price is £222
includes taxes & fees
6 Jul - 7 Jul
Guesthouse at Norwalk Inn

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (16)
"The covered parking was really helpful on a cold day."
Luxury Apartments by Hyatus at The Asher

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (3)
"This house was perfect for our visit. It was clean and comfortable and provided everything we needed. Walking distance to a restaurant, coffee shop and the best ice cream! Would definitely stay here again. "
Minutes to Walnut Beach, newly renovated 3 bedroom home

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (6)
"Property manager was very attentive to our needs and replied to all msgs in a very timely fashion. There were a couple things that needed tending to when we arrived and he took care of it immediately. Despite having parking on the street, it was never an issue and often got the spot that was right next to the house. The beach was directly across the street and was clean with friendly neighbors! Although there is a sign stating no dogs or animals allowed on the beach, there were many dogs on the...
The price is £425
includes taxes & fees
5 Jul - 6 Jul
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

8.0 out of 10, Very good, (2)
"It was beautiful and quite. A hidden gem."
The price is £230
includes taxes & fees
1 Jul - 2 Jul
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

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

9.0 out of 10, Wonderful, (7)
"This property is well maintained. Some amenities available that made our stay more enjoyable. My only issue was the amount of noise you could hear throughout the night.but once you're asleep it doesn't matter. "
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Main Street Westport, walk to shops, dining, downtown

8.0 out of 10, Very good, (1)
"It’s a good house - very basic - but gets job done - tricky driveway & noise from road is thing - we did not spend much time in house so was not much of factor Property managers were very helpful supportive"
Main Street Westport, walk to shops, dining, downtown

My favorite place!

2.0 star property
My favorite place!

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

9.4 out of 10, Exceptional, (91)
"This is a beautiful home even if you live in the area and just want to spend the weekend at the lake, it’s a perfect getaway. We love that it was dog friendly. The host was wonderful and very accommodating. The house came stocked with everything that you would need for a perfect stay. "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

SALTY KISSES COZY BEACH HOUSE /BEACH ACCESS ACROSS STREET WATER VIEW

2.0 star property
10.0 out of 10, Exceptional, (2)
"The house is absolutely perfect. Location, cleanliness, beach amenities, owner communication, etc. I’ve stayed at 30+ VRBO/Aribnb properties over the last decade and this is by far one of my top 2. Denise was so nice and accommodating and even had restaurant & entertainment suggestions. The house, the yard, garage, bikes, beach chairs, umbrella, kayaks, fire pit…it all made our stay so wonderful. We will absolutely be back. "
SALTY KISSES COZY BEACH HOUSE /BEACH ACCESS ACROSS STREET WATER VIEW

Beach house in Milford, CT

The price is £558
includes taxes & fees
6 Jul - 7 Jul
Beach house in Milford, CT

Modern House in Black Rock

2.0 star property
9.0 out of 10, Wonderful, (6)
"Very easy stay and great location convenient to Fairfield University . Plenty of options to walk to for coffee or meals. Had everything we needed. Clean, well equipped. Great communication with owners. "
Modern House in Black Rock

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

9.4 out of 10, Exceptional, (43)
"If we are ever in the area again we would love to stay here again if available. "
The price is £214
includes taxes & fees
14 Jul - 15 Jul
The Safe House - High Tech Apt #2 - 3 Beds

Candlewood Lake Retreat

10.0 out of 10, Exceptional, (2)
"Excellent facilities at this great property. Really good outdoor deck, good sized bedrooms, huge tv next to the table football in the basement, really good kitchen facilities. The host Raymond was very helpful, and Uber happy to bring you home if need be."
Candlewood Lake Retreat

Modern Courtland

2.0 out of 10, (1)
The price is £285
includes taxes & fees
1 Jul - 2 Jul
Modern Courtland

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (42)
"Had an amazing stay. House was stocked with all of the essentials. Fantastic location. Would definitely stay again!"
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
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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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 Levitt Pavilion 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.