Weston Vacation Rentals

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Vacation Rentals in Weston

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (36)
"beautiful cottage with all the amenities you need.. charming historic property.. would highly recommend "
The price is CA $280
CA $436 total
includes taxes & fees
Jan 11 - Jan 12
Adorable 1-Bedroom Cottage in Weston, CT

Stamford Suites

2.5 star property
6.8 out of 10, (773)
"It was in walking distance of the event we were going to."
The price is CA $202
CA $232 total
includes taxes & fees
Jan 21 - Jan 22
Stamford Suites

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (46)
"Place was clean and comfortable. Some nights were louder than others with by passers from the bar next door. Otherwise pleasant visit. Could not get in the first night. Needed to get another hotel stay. Was not able to reach anyone."
The price is CA $307
CA $498 total
includes taxes & fees
Jan 17 - Jan 18
DUNE Fairfield Beach

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 CA $108
CA $194 total
includes taxes & fees
Jan 12 - Jan 13
Business or Weekend escape

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

9.6 out of 10, Exceptional, (80)
"Thank you for allowing us to reside at your beautiful property. We appreciate your expedited communication & commitment to quality. We thank Jehovah for a safe enjoyable trip & as we return back to Atlanta, GA. "
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

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

10.0 out of 10, Exceptional, (116)
"Enjoyed the theater room and the comfortable bed"
Lower Lvl Private 2BR/1BA Family/Pet Friendly

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

9.4 out of 10, Exceptional, (87)
"The parking situation was a bit tricky because there was no good way to back in. Other than that, location was great - cute area! "
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

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

9.6 out of 10, Exceptional, (17)
"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 CA $213
CA $597 total
includes taxes & fees
Jan 11 - Jan 12
Luxury Designer 2 bedroom+office/3bed vacation home.

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

9.8 out of 10, Exceptional, (27)
"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

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 CA $704
CA $1,024 total
includes taxes & fees
Jan 11 - Jan 12
Westport Paradise With Every Amenity!

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (26)
"Wonderful little bungalow. Owners are really nice and responsive. House is well maintained, cleaned and better stocked than any other rental we've been in. Thank you!!"
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

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 CA $401
CA $461 total
includes taxes & fees
Jan 26 - Jan 27
Guesthouse at Norwalk Inn

(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

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

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

9.8 out of 10, Exceptional, (43)
"Property worked out great for us"
The price is CA $145
CA $293 total
includes taxes & fees
Jan 15 - Jan 16
The Safe House - High Tech Apt #3 - 4 beds

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (25)
"Great communication and accommodations from the host. We were in town for a concert and the location couldn't have been better! Would recommend this stay for anyone looking within the area."
Cheerful 4 bedrooms residential house.

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

10.0 out of 10, Exceptional, (29)
"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 #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 CA $145
CA $296 total
includes taxes & fees
Jan 14 - Jan 15
The Safe House - High Tech Apt #2 - 3 Beds

Studio OSM · Sunny Westport Studio Apt. Above Historic Mill

10.0 out of 10, Exceptional, (68)
"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.
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Other types of properties in Weston you may be interested in

EVEN Hotel Norwalk, an IHG Hotel

3.5 star property
8.2 out of 10, Very good, (1003)
"Staff was super helpful my son is disabled and I needed some changes and staff did all they could to help"
The price is CA $147
CA $169 total
includes taxes & fees
Jan 12 - Jan 13
EVEN Hotel Norwalk, an IHG Hotel

Amsterdam Hotel

2.0 star property
8.4 out of 10, Very good, (1531)
"Convenient"
The price is CA $144
CA $167 total
includes taxes & fees
Jan 12 - Jan 13
Amsterdam Hotel

Hyatt Regency Greenwich

4.0 star property
7.8 out of 10, Good, (1006)
"It was good for families. "
The price is CA $255
CA $294 total
includes taxes & fees
Feb 7 - Feb 8
Hyatt Regency Greenwich
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.

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?

Lower Lvl Private 2BR/1BA Family/Pet Friendly: This vacation home rental outside of Weston offers a patio, a terrace, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker. You and your friends and family can relax into your vacation with amenities like a garden.

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 Norwalk City Hall 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.