Weston Vacation Rentals

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Vacation Rentals in Weston

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (6)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (37)
"Lovely cottage! VERY convenient location for our purposes. An issue with the shower not draining was a disappointment. "
The price is CA $271
CA $423 total
includes taxes & fees
Apr 20 - Apr 21
Adorable 1-Bedroom Cottage in Weston, CT

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (52)
"All good"
The price is CA $309
CA $432 total
includes taxes & fees
Apr 17 - Apr 18
DUNE Fairfield Beach

Stamford Suites

3.0 star property
5.8 out of 10, (27)
"Convenience. Full kitchen and spacious rooms"
The price is CA $237
CA $273 total
includes taxes & fees
Apr 30 - May 1
Stamford Suites

Business or Weekend escape

9.6 out of 10, Exceptional, (34)
"Very nice owner with great communication. "
The price is CA $104
CA $188 total
includes taxes & fees
Apr 17 - Apr 18
Business or Weekend escape

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (15)
"Perfect location. Great service. Amenities pretty cool "
Luxury Apartments by Hyatus at The Asher

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 $388
CA $446 total
includes taxes & fees
May 12 - May 13
Guesthouse at Norwalk Inn

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (30)
"Donna is a wonderful attentive host. We felt very welcomed in Donna’s home. It was a wonderful location for a mother daughter get away. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

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

9.4 out of 10, Exceptional, (88)
"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!

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (106)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (30)
"Toocold in Connecticut, host was alway inclose contact, heat was our only issue "
Cheerful 4 bedrooms residential house.

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

9.4 out of 10, Exceptional, (18)
"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 CA $220
CA $605 total
includes taxes & fees
Apr 17 - Apr 18
Luxury Designer 2 bedroom+office/3bed vacation home.

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

9.8 out of 10, Exceptional, (28)
"Our family's stay at Helen and Richie's property for the holidays was perfect. Waking up to views of the lake every morning, watching flocks of birds travel on the water and being surrounded by nature was all we could ask for. The house has all amenities provided in the kitchen, bathrooms etc. Location is convenient near shops, grocery, and restaurants in New Fairfield. The hosts were very responsive in communication and I appreciated them providing everything we needed. "
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Cozy Cabin @ Sticks & Stones Farm

7.6 out of 10, Good, (4)
"Nice clean cabin. Good communication with host."
The price is CA $132
CA $264 total
includes taxes & fees
Apr 21 - Apr 22
Cozy Cabin @ Sticks & Stones Farm

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (19)
"This is a beautiful property. When we arrived, everything was perfect. It is completely stocked, including games for the family, and an unbelievable view of the lake. Communication with the homeowner was wonderful and we definitely plan to come back. We highly recommend this beautiful, clean and well kept home on the lake!."
Lakeside luxury: beautiful, relaxing 4 bedroom home

The Cozy Studio

9.0 out of 10, Wonderful, (4)
"great apartment, bedroom is NOT separated from living room lounge area. Parking is not easy peasy but there are spots within a block or 2 no worries. Noise from people staying in unit above this one can a bit jarring, especially if you are on different schedules, we worked it out no problem. Decent pizza and latin food just around the corner."
The Cozy Studio

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (116)
"The Arts and Crafts home was more beautiful than the pictures reflected! We loved all of the details in the woodwork, hidden little corners, tons of space to spread out and wonderful places to gather together. Having recently sold our "family home" we were thrilled to find this home in which to have a mini- family reunion. The kitchen was incredibly well-stocked- from serving platters to garlic powder to paper towels...We had everything we needed. The gas fireplace created a beautiful focal...
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

1ST FLR APT Your Private Resort, now FAMILY-ized: 1 BR + LR suitable for 2 kids

9.4 out of 10, Exceptional, (56)
"This was an amazing trip for me and my wife to enjoy a nice private get away. The property was very clean. The owner Gabe was very friendly and kind their dogs were a delight and very playful happy dogs. The experience overall was very nice for both of us."
1ST FLR APT Your Private Resort, now FAMILY-ized: 1 BR + LR suitable for 2 kids

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

9.8 out of 10, Exceptional, (45)
"Had a fun filled weekend and this was the serving time staying here but in a different apartmentVery close to the Capital Theater in Port Chester Excellent restaurants near the theater and we discovered an amazing Asian restaurant within a 5 minute walk"
The Safe House - High Tech Apt #3 - 4 beds

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

9.2 out of 10, Wonderful, (20)
"The best part of the stay was fun with family because of the mini pool table/air hockey and darts. Kids loved it! "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
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

Amsterdam Hotel

2.0 star property
8.4 out of 10, Very good, (1581)
"Eric S."
The price is CA $117
CA $136 total
includes taxes & fees
May 4 - May 5
Amsterdam Hotel

EVEN Hotel Norwalk by IHG

3.5 star property
8.2 out of 10, Very good, (1000)
"It was pretty gd "
The price is CA $165
CA $190 total
includes taxes & fees
Apr 20 - Apr 21
EVEN Hotel Norwalk by IHG

Hyatt Regency Greenwich

4.0 star property
8.0 out of 10, Very good, (841)
"Great staff, bar was fantastic."
The price is CA $232
CA $267 total
includes taxes & fees
May 1 - May 2
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?

Business or Weekend escape: This vacation home rental outside of Weston is equipped with a barbecue grill, 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 vacation rentals are there in Weston?

Choose from 13 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.