Book a Weston Cottage

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
3 Oct - 5 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec
In four months
9 Jan - 11 Jan

Featured Cottages in Weston

Adorable Beach Cottage
Exterior

Adorable Beach Cottage

10.0 out of 10, Exceptional, (48)
"This property is perfect for two or 3 adults. Charming cottage, very clean, great beach community. "
Adorable Beach Cottage
Charming 3 Bedroom Beach Front Cottage
Outdoor dining

Charming 3 Bedroom Beach Front Cottage

2.0 star property
10.0 out of 10, Exceptional, (4)
"Stayed here while attending the Soundside Fest. Perfect location to be away from the busy Bridgeport area. The water is right there and it’s the perfect space for a weekend get away."
Charming 3 Bedroom Beach Front Cottage
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Beach nearby

Renovated Milford Beach home by Charles Island/Silver Sands Pk

10.0 out of 10, Exceptional, (6)
"This place was perfection for my mom and I. The location was easy to get to from highway, the inside of the place was spotless, updated and cozy and property owner Susana was highly responsive to any questions we had. The location was ideal for walks both on the beach and on walking paths. We will definitely stay again in the future. "
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Cos Cob Cottage- Full Kitchen, Pet Friendly
Exterior

Cos Cob Cottage- Full Kitchen, Pet Friendly

10.0 out of 10, Exceptional, (4)
"2 night stay over Thanksgiving holiday. Cozy Cottage was just lovely. Fully applianced and stocked kitchen. Large bathroom-super soft towels. King size bed was comfy and cozy. Living room was perfect for relaxing. Rules clearly communicated. Owners were very helpful and responsive. Driveway a little tricky to maneuver when parking spots are occupied. Safe location…. Good walking and exploring in the area "
Cos Cob Cottage- Full Kitchen, Pet Friendly
Westport "Gold Coast" across from Southport beach
Exterior

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (92)
"Easy communication, clean apartment, good location for beach and nearby towns. "
Westport "Gold Coast" across from Southport beach
Second floor cottage apartment located in a private community.
Exterior

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (16)
"Great time, nice little private neighborhood! Pretty views if you go for nice walks. 2 great parks near by. Lovely stay. Had everything we needed "
Second floor cottage apartment located in a private community.
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Exterior

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

10.0 out of 10, Exceptional, (9)
"Wonderful stay!"
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Fridge, microwave, oven, stovetop

Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT

10.0 out of 10, Exceptional, (8)
"Great relaxing stay quite and comfortable "
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Beach cottage on private beach!
Exterior

Beach cottage on private beach!

10.0 out of 10, Exceptional, (4)
"It was a very nice cottage. Great price for staying right on the beach"
Beach cottage on private beach!
Beachfront Connecticut Retreat w/ Views!
Interior

Beachfront Connecticut Retreat w/ Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great spot on the ocean with an amazing host!"
Beachfront Connecticut Retreat w/ Views!
Charming Studio-Cottage with WiFi & TV free parking in Greenwich
Exterior

Charming Studio-Cottage with WiFi & TV free parking in Greenwich

Charming Studio-Cottage with WiFi & TV free parking in Greenwich
Trendy 1 bedroom +loft apartment w/ parking
Smart TV

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (12)
"Perfect for my needs. Would stay again for sure"
Trendy 1 bedroom +loft apartment w/ parking
Bright Milford Beach House w/ Outdoor Shower
House (2 Bedrooms) | Interior

Bright Milford Beach House w/ Outdoor Shower

3.0 star property
Bright Milford Beach House w/ Outdoor Shower
Lakefront Brewster Vacation Rental w/ Private Dock
Cottage (3 Bedrooms) | Interior

Lakefront Brewster Vacation Rental w/ Private Dock

3.0 star property
Lakefront Brewster Vacation Rental w/ Private Dock
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Property grounds

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

2.0 star property
10.0 out of 10, Exceptional, (3)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Beachfront cottage located in the heart of Fairfield Beach!!
Outdoor dining

Beachfront cottage located in the heart of Fairfield Beach!!

9.6 out of 10, Exceptional, (18)
"I grew up here! Always fun"
Beachfront cottage located in the heart of Fairfield Beach!!
New Fairfield Vacation Rental w/ Lake Views!
Property grounds

New Fairfield Vacation Rental w/ Lake Views!

3.0 star property
New Fairfield Vacation Rental w/ Lake Views!
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Outdoor dining

Charming Fairfield Beach 3BR 2BA Cottage By The Sea

10.0 out of 10, Exceptional, (33)
"Clean, quaint spot for a family gathering. A little chilly in February but very calming and pleasant stay."
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Sun and Fun on the beach!!
Outdoor dining

Sun and Fun on the beach!!

9.6 out of 10, Exceptional, (17)
"Perfect beach and outdoor life for young kids! Such a great relaxing long weekend - the house had everything we needed. Hoping for another stay soon!"
Sun and Fun on the beach!!
Summer Escape on Candlewood Lake – Private Beach, Hot Tub & Cozy Cottage!
Exterior

Summer Escape on Candlewood Lake – Private Beach, Hot Tub & Cozy Cottage!

10.0 out of 10, Exceptional, (1)
"Lovely little 2/2 house in a great location with just about everything we needed. Very quiet too. Our host, Jonathan was very responsive when we had questions or concerns. We would highly recommend!"
Summer Escape on Candlewood Lake – Private Beach, Hot Tub & Cozy Cottage!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Weston Hotel Reviews

Microtel Inn & Suites by Wyndham Bethel/Danbury

Microtel Inn & Suites by Wyndham Bethel/Danbury

10/10 Excellent
"Great value. "
Gerald J. 1-night trip
Posted 2 days ago
Microtel Inn & Suites by Wyndham Bethel/Danbury

Find out more about Weston

Find out more about Weston

Weston Cottages information

Number of reviews
256
Accommodation
59 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Weston cost?
You can expect to pay between and per night for cottages in Weston. Whatever your budget, a wonderful stay is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Weston?
Pick from 59 cottages in Weston. Whether you're holidaying with the family or planning a weekend retreat with your best buds, Expedia will help you find the ideal space to immerse yourself in nature.
What is there to do in Weston near my cottage?
If you want to discover the sights of Weston, be sure to stop by Lucius Pond Ordway / Devil's Den Preserve. It's popular with locals and visitors alike.