Weston Holiday Rentals

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Check prices for these dates

Tonight
18 Apr - 19 Apr
Tomorrow
19 Apr - 20 Apr
This weekend
18 Apr - 20 Apr
Next weekend
25 Apr - 27 Apr

Holiday Rentals in Weston

Historic Connecticut Home w/ Grill & Spacious Yard
Microwave, stovetop, dishwasher, coffee/tea maker

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
Fridge, microwave, oven, stovetop

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 HK$1,514
HK$2,331 total
includes taxes & fees
21 Apr - 22 Apr
Adorable 1-Bedroom Cottage in Weston, CT
DUNE Fairfield Beach
Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (52)
"Absolutely perfect location for visiting Fairfield University! Everything about it exceeded our expectations."
The price is HK$1,728
HK$2,415 total
includes taxes & fees
27 Apr - 28 Apr
DUNE Fairfield Beach
Stamford Suites
Lobby

Stamford Suites

3.0 star property
5.8 out of 10, (27)
"Convenience. Full kitchen and spacious rooms"
The price is HK$1,460
HK$1,678 total
includes taxes & fees
20 Apr - 21 Apr
Stamford Suites
Business or Weekend escape
Pool

Business or Weekend escape

9.6 out of 10, Exceptional, (34)
"Very nice owner with great communication. "
The price is HK$582
HK$1,048 total
includes taxes & fees
20 Apr - 21 Apr
Business or Weekend escape
Luxury Apartments by Hyatus at The Asher
Lounge

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (15)
"The apartment was amazing. It was spacious, clean, incredibly comfy bed (although it made early mornings a problem!). The check in process was really easy. I also love the fact there is a huge washer and dryer so was able to do some washing mid-stay and not have to fill my suitcase up too much. The Gym was great and not too busy so was able to use the equipment I wanted to. I had a question one evening and emailed Hyatus expecting an answer the next day and they came back with a very helpful...
Luxury Apartments by Hyatus at The Asher
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
Exterior

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!
Guesthouse at Norwalk Inn
Property entrance

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 HK$2,166
HK$2,491 total
includes taxes & fees
12 May - 13 May
Guesthouse at Norwalk Inn
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Fridge, microwave, oven, stovetop

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

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 HK$1,227
HK$3,344 total
includes taxes & fees
21 Apr - 22 Apr
Luxury Designer 2 bedroom+office/3bed vacation home.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Exterior

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

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
Cozy Cabin @ Sticks & Stones Farm
Terrace/patio

Cozy Cabin @ Sticks & Stones Farm

7.6 out of 10, Good, (4)
"Nice clean cabin. Good communication with host."
The price is HK$738
HK$1,475 total
includes taxes & fees
21 Apr - 22 Apr
Cozy Cabin @ Sticks & Stones Farm
The Cozy Studio
Fridge, microwave, oven, stovetop

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
Exterior

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
Lakeside luxury: beautiful, relaxing 4 bedroom home
Property grounds

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

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
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Terrace/patio

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Lake house cozy to relax with a family. 6 bedroom very spacious house.
Minutes to Walnut Beach, newly renovated 3 bedroom home
Fridge, microwave, oven, stovetop

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (2)
"Cute little place that was perfect to walk to the wedding venue. Communication with the host was perfect and very helpful."
Minutes to Walnut Beach, newly renovated 3 bedroom home
Cheerful 4 bedrooms residential house.
Exterior

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.
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 by IHG
Individually decorated, individually furnished, desk, laptop workspace

EVEN Hotel Norwalk by IHG

3.5 star property
8.2 out of 10, Very good, (1005)
"It was pretty gd "
The price is HK$785
HK$903 total
includes taxes & fees
20 Apr - 21 Apr
EVEN Hotel Norwalk by IHG
Amsterdam Hotel
View from property

Amsterdam Hotel

2.0 star property
8.4 out of 10, Very good, (1585)
"Very clean, feels like I stepped through a time machine back to the seventies with the red carpet and decor, but if this is original carpet they've been taking amazing care of it because it looks brand new! The rooms were very very clean which was the most important to me, and this is probably the cleanest I've ever seen a hotel that is this old. The staff is amazing they're very nice, had an issue and double booked it by accident throughhotels.com, and the front desk guy in the evening was very...
The price is HK$668
HK$775 total
includes taxes & fees
22 Apr - 23 Apr
Amsterdam Hotel
Hyatt Regency Greenwich
2 bars/lounges

Hyatt Regency Greenwich

4.0 star property
8.0 out of 10, Very good, (844)
"Room was classic 2queen All parts were not shop worn Pleasant desk "
The price is HK$1,296
HK$1,491 total
includes taxes & fees
1 May - 2 May
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 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.