Weston Vacation Rentals

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Vacation Rentals in Weston

Stamford Suites

4.0 star property
5.6 out of 10, (47)
"You walk 2 blocks and bunch of stores and great restaurants. Try Bari restaurant"
The price is CA $232
CA $267 total
includes taxes & fees
Jul 27 - Jul 28
Stamford Suites

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (61)
"Incredible staff, friendly, helpful. "
The price is CA $230
CA $349 total
includes taxes & fees
Aug 14 - Aug 15
DUNE Fairfield Beach

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 CA $371
CA $427 total
includes taxes & fees
Aug 20 - Aug 21
Guesthouse at Norwalk Inn

Business or Weekend escape

9.2 out of 10, Wonderful, (42)
"Very nice owner with great communication. "
The price is CA $116
CA $200 total
includes taxes & fees
Aug 3 - Aug 4
Business or Weekend escape

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

10.0 out of 10, Exceptional, (5)
The price is CA $519
CA $951 total
includes taxes & fees
Aug 11 - Aug 12
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.2 out of 10, Wonderful, (15)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

(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

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.2 out of 10, Wonderful, (24)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

10.0 out of 10, Exceptional, (1)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
The price is CA $155
CA $269 total
includes taxes & fees
Jul 28 - Jul 29
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

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

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

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

10.0 out of 10, Exceptional, (1)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
The price is CA $987
CA $1,894 total
includes taxes & fees
Jul 27 - Jul 28
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

8.6 out of 10, Excellent, (7)
"I rented this place because of the location and convenience to the many things we enjoy about Milford CT. The master bedroom is top-notch as well as the living space downstairs. We hoped to use the outdoor fire place make smores, but due to a medical emergency our trip was cut short. Regardless, we enjoyed our stay at 42 Wood Ave. Thank you, Tiffany, for supplying an awesome rental."
The price is CA $377
CA $626 total
includes taxes & fees
Jul 31 - Aug 1
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (25)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

My favorite place!

2.0 star property
2.0 out of 10, (1)
My favorite place!

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

10.0 out of 10, Exceptional, (79)
"We stayed for a birthday weekend with a few other couples and had a great time. There is plenty of space for everyone to spread out and each 'area' of the house is incredibly comfortable (especially the movie theater). If you need anything there are plenty of stores close by and the area is very safe. Overall, no complaints and would recommend to anyone looking for a getaway."
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

Renovated 2BR Retreat / Modern Comforts Included

10.0 out of 10, Exceptional, (1)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
The price is CA $253
CA $536 total
includes taxes & fees
Aug 12 - Aug 13
Renovated 2BR Retreat / Modern Comforts Included

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

8.8 out of 10, Excellent, (6)
The price is CA $216
CA $421 total
includes taxes & fees
Jul 27 - Jul 28
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

My little place Cozy Open concept for quiet time.

8.0 out of 10, Very good, (2)
"Great, clean property that was easy to access and very convenient to downtown Bridgeport. Perfect place to clean up and sleep. Very welcoming space."
The price is CA $203
CA $673 total
includes taxes & fees
Aug 7 - Aug 8
My little place Cozy Open concept for quiet time.
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

Frequently asked questions

Can I find a vacation rental in Weston?

Yes, there are vacation rentals close to well known attractions in Weston, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals that Weston has to offer?

Business or Weekend escape: This vacation home rental outside of Weston is equipped with a barbecue grill, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave, and a coffee maker.

How many vacation rentals are there in Weston?

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

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 larger area.

What’s a vacation rental in Weston like?

Vacation rentals are private properties you can reserve for a short or long stay in Weston. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.