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Compare 50 Cottages in Weston with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (5)
"We had a wonderful stay and this house did not disappoint! The home is very well appointed and has everything you need. Property is very clean and would recommend this home to anyone visiting this area. Will definitely be coming back!"
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Private Beach 100 yards from Cottage

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

9.4 out of 10, Exceptional, (86)
"Perfectly adorable house that was ideal for our brief getaway. I wish we had been able to use the kayak/canoe but time was tight. The only issue was the driveway which had me holding my breath a bit but luckily we were careful and managed without incident."
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Property grounds

Sweet Dotti's Cottage on Candlewood Lake - 60M NYC

9.6 out of 10, Exceptional, (14)
"Landscaping was spectacular and we enjoyed a beautiful view of the lake. Baths and bedrooms very clean. Plenty of charging ports. Terrible mold and mildew smell in lower level. Number of hazards noted, handrail missing on stairs, no lights on outdoor stairway, thermostat access by leaning over the stairs. The property needs a good deep cleaning."
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Trendy 1 bedroom +loft apartment w/ parking
Interior

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (4)
"This was our home base while we explored NYC. The place was lovely and well-appointed. It’s almost a shame that we hardly spent any time there. Just in and out to sleep, shower and eat breakfast, then back to the commuter train into NYC. Found free unlimited street parking a few blocks from the train station. Appreciated access to laundry on our last morning to start the next leg of our trip with fresh clothes. "
Trendy 1 bedroom +loft apartment w/ parking
Fairfield Cottage · Charming Fairfield Cottage By The Sea

Fairfield Cottage · Charming Fairfield Cottage By The Sea

10.0 out of 10, Exceptional, (31)
"What a wonderful find, and only an hour away from NYC. Fairfield CT is beautiful, friendly people, great restaurants, dog friendly, beautiful private beach, the list goes on and on. Thank you to Gerard for being so helpful, kind and always there to answer any questions, and give great recommendations. If you ever need a break from the city, this is the place to go to. Thanks again for such a wonderful holiday! We will be back."
Fairfield Cottage · Charming Fairfield Cottage By The Sea
Beach cottage on private beach!
Beach

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!
Adorable 1-Bedroom Cottage in Weston, CT
Living-Room view from Mezzanine

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (33)
"This cottage is so beautiful, well equipped and comfortable. The hosts were welcoming, accommodating and checked in with us to make certain we were enjoying our visit. The gorgeous location was perfect for us. We were visiting family in the area which is why we chose it. We didn’t realize how near it was to quaint towns, great restaurants, etc. We also spent an afternoon at nearby Sherwood Island followed by lobster rolls at a nearby restaurant. Thank you! Looking forward to a return visit! "
The price is AED 716
AED 1,114 total
includes taxes & fees
25 Nov - 26 Nov
Adorable 1-Bedroom Cottage in Weston, CT
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Beach

Renovated Milford Beach home by Charles Island/Silver Sands Pk

10.0 out of 10, Exceptional, (2)
"Our family of 4 stayed comfortably. Towels and sheets were well stocked. We loved walking across to the beach. Our 10 year old could take our 5 year old. We biked on street and sidewalks to downtown Milford, public library, playground. We loved Pennys used books. It was such a relaxing trip and we will be back to stay at Susana's lovely place."
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Westport "Gold Coast" across from Southport beach
Property grounds

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (82)
"The property was perfectly located for my needs, nicely appointed, comfortable furnishings, spacious, nice light, and felt like home."
Westport "Gold Coast" across from Southport beach
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Exterior

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

9.4 out of 10, Exceptional, (3)
"I spent 2 serene weeks here and hope to return some day! With modern creature comforts in the kitchen, the rest of this home is very rustic. If you are looking for peace and quiet, and are into drawing, cooking or reading books to the sounds of trees rustling and water flowing across the street, you will be in heaven here. For summer months, note that there is only a small portable AC unit in the sunroom. There are several fans and it was manageable in early summer, but I imagine it is quite...
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Beachfront Connecticut Retreat w/ Views!
Milford Vacation Rental | 3BR | 1.5BA | 832 Sq Ft | Steps to Access

Beachfront Connecticut Retreat w/ Views!

9.6 out of 10, Exceptional, (7)
"Just a wonderful beach cottage in a great spot that had all we needed"
Beachfront Connecticut Retreat w/ Views!
🔥Fairfield County Cozy cottage , super close great adventure
Living area

🔥Fairfield County Cozy cottage , super close great adventure

9.8 out of 10, Exceptional, (6)
"Comfortable house, not huge, but nicely decorated. Host was very quick to respond when I had trouble with door code. The only con for us was lack of handrails on steps to exterior doors (front and back). Otherwise a great place to stay."
🔥Fairfield County Cozy cottage , super close great adventure
Second floor cottage apartment located in a private community.
Living Room with view towards Bedroom 1

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (14)
"What a lovely apartment hidden away on a private street. It is very clean and well-kept, and extra attention is given to making sure guests have what they need. Communication with hosts was easy and straightforward. We were very pleased with our stay. "
Second floor cottage apartment located in a private community.
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, (15)
"This is my third year staying at this property. I have friends that live around the area so it is a nice quiet private space to reconnect. Paul the host is always quick to respond to any concerns I may have while staying. My dog Angel is in heaven literally 5 steps to the water . The beach and people are so kind and friendly. Love it!"
Beachfront cottage located in the heart of Fairfield Beach!!
Bright Milford Beach House w/ Outdoor Shower
Living area

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
Brewster Vacation Rental | 3BR | 2BA | Stairs Required | 2,600 Sq Ft

Lakefront Brewster Vacation Rental w/ Private Dock

10.0 out of 10, Exceptional, (3)
"Family trip consisting of 2 grandparents, 2 parents, and 1 adult grandchild went off without a hitch. The property is so beautiful- meticulously clean house, soft beds and luxury bedding, top notch kitchen appliances, with the most peaceful view of the lake. Excellent communication from host, including helpful welcome book. Fresh loaf of cranberry bread from local farmer’s market was a nice touch. DeCicco’s Market was our go-to for groceries / wish we had one of those at home. Enjoyed...
Lakefront Brewster Vacation Rental w/ Private Dock
California cozy cottage/studio in the middle of the Greenwich
Outdoor dining

California cozy cottage/studio in the middle of the Greenwich

10.0 out of 10, Exceptional, (1)
"This VRBO was a pleasure! Host Olga was very accommodating. This was my first VRBO experience and I will definitely do this again. So much nicer than a hotel stay. It was a wonderful 5 days! I would highly recommend Olga and her California Cottage. "
California cozy cottage/studio in the middle of the Greenwich
Sun and Fun on the beach!!
You are here!

Sun and Fun on the beach!!

9.6 out of 10, Exceptional, (15)
"Very good place on the beach….and beach walking Paul communication was very timely"
Sun and Fun on the beach!!
South Salem Vacation Rental w/ Furnished Deck!
South Salem Vacation Rental | 1BR | 1BA | Stairs Required | 950 Sq Ft

South Salem Vacation Rental w/ Furnished Deck!

10.0 out of 10, Exceptional, (1)
"Everything was easy and fine at the space. I had to stay for family reasons - so "location" was the most important factor to me. The worst thing in the unit is that the spiral stair is narrow - and a fat person or person with bad knees is NOT going to be using that stairwell easily. Otherwise, the unit had everything I needed and was perfectly appointed for an easy weekend stay. Enjoy!"
South Salem Vacation Rental w/ Furnished Deck!
Charming West Haven Home - Walk to Beach!
Living area

Charming West Haven Home - Walk to Beach!

3.0 star property
Charming West Haven Home - Walk to Beach!
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 property types in Weston

Adorable 1-Bedroom Cottage in Weston, CT
Living-Room view from Mezzanine

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (33)
"This cottage is so beautiful, well equipped and comfortable. The hosts were welcoming, accommodating and checked in with us to make certain we were enjoying our visit. The gorgeous location was perfect for us. We were visiting family in the area which is why we chose it. We didn’t realize how near it was to quaint towns, great restaurants, etc. We also spent an afternoon at nearby Sherwood Island followed by lobster rolls at a nearby restaurant. Thank you! Looking forward to a return visit! "
The price is AED 716
AED 1,114 total
includes taxes & fees
25 Nov - 26 Nov
Adorable 1-Bedroom Cottage in Weston, CT
Stamford Suites
Property amenity

Stamford Suites

2.5 star property
6.8 out of 10, (766)
"All is well"
The price is AED 528
AED 591 total
includes taxes & fees
29 Nov - 30 Nov
Stamford Suites
Business or Weekend escape
A Queen Size Bed for Two Persons and Also Queen Size Sofa Bed for Two Persons.

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 AED 294
AED 517 total
includes taxes & fees
26 Nov - 27 Nov
Business or Weekend escape
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

How much do cottages in Weston cost?
You’ll pay between AED 716 and AED 716 per night for cottages in Weston. No matter your budget, a wonderful stay is just clicks 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?
Pack your suitcase and pick from 50 cottages in Weston. Imagining a place where you can relax and stay in touch with nature? Expedia can help you find the ideal escape in only a click or two.
Why book your cottage in Weston with Expedia?
Booking a cottage in Weston is as easy as clicking on your travel dates and choosing an ideal place for a getaway in the outdoors. From upmarket retreats to low-cost properties and cottages that come with amenities like a kitchenette, Expedia has something for all tastes and styles. As for irresistible deals? We’ve have them as well!
How can I find cheap cottages in Weston?
The easiest way to score cheap cottages in Weston is with Expedia’s useful filter tool. Tailor your search results by star rating, amenities and budget to take advantage of awesome rates in a couple of clicks.