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Compare 51 Cottages in Weston with updated reviews, rates, and availability.

Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Beach nearby, beach towels
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
9.4 out of 10, Exceptional, (82)
"Property was clean, well appointed, wish we could have stayed a bit longer to enjoy more of the lake & fire pit! "
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Trendy 1 bedroom +loft apartment w/ parking
Smart TV
Trendy 1 bedroom +loft apartment w/ parking
10.0 out of 10, Exceptional, (1)
"My husband and I are relocating to the East Coast and after a week-long drive across the country, we were happy, tired and grateful to arrive at Leti’s lovely apartment for a 3-week stay. It was exactly what we had hoped for —in fact, better than expected. The unit had parking, a fenced yard (with patio table and grassy area), a washer-dryer (with soap provided!) and a wonderful, well-appointed full kitchen and living space. The apartment was extremely clean with new furnishings and...
Trendy 1 bedroom +loft apartment w/ parking
Adorable 1-Bedroom Cottage in Weston, CT
Fridge, microwave, oven, stovetop
Adorable 1-Bedroom Cottage in Weston, CT
10.0 out of 10, Exceptional, (30)
"Very cozy cottage a little off the beaten path in Weston. Quiet & stocked with amenities for our comfort. The owner was helpful & responsive. If there was any drawback it would be helpful to air out the cottage as its an old building & investing in some new pillows would be appreciated by the next guests. Otherwise a great stay."
The price is ￥28,051
￥43,767 total
includes taxes & fees
Sep 24 - Sep 25
Adorable 1-Bedroom Cottage in Weston, CT
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
Fairfield Cottage · Charming Fairfield Cottage By The Sea
Fridge, microwave, oven, stovetop
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 nearby, sun loungers, beach towels
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!
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, (1)
"Great relaxing stay quite and comfortable "
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Cozy Country Cottage
TV, fireplace
Cozy Country Cottage
2.0 star property
8.8 out of 10, Excellent, (3)
"Get away from the hustle and bustle with this cute country cottage. Queen beds in the first floor and super cool loft, nice updates in the bathroom and kitchen. Window A/C units kept us cool on one of the hottest weeks of the year. Close to Derby and Route 15 made this a super-convenient stop-over for us as we came back from our honeymoon!"
Cozy Country Cottage
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Property grounds
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
10.0 out of 10, Exceptional, (1)
"Charming cottage, beautiful location, wonderful hosts! Located on a beautiful stretch of river and near outstanding running and hiking.Highly recommend."
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Smart TV
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
Exterior
Westport "Gold Coast" across from Southport beach
10.0 out of 10, Exceptional, (79)
"Very cute spot in a great location. "
Westport "Gold Coast" across from Southport beach
Charming Private and Serene cottage close to I-84 and shopping
Exterior
Charming Private and Serene cottage close to I-84 and shopping
The price is ￥35,963
￥64,805 total
includes taxes & fees
Oct 16 - Oct 17
Charming Private and Serene cottage close to I-84 and shopping
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Smart TV, computer monitors, printers
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!
Property grounds
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
Fridge, microwave, oven, stovetop
🔥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.
Fridge, microwave, oven, stovetop
Second floor cottage apartment located in a private community.
9.4 out of 10, Exceptional, (13)
"The cottage was as described and the photos don’t really do it justice, it is lovely and the location cannot be beat. We had good communication with the hosts and overall it was a very nice stay. Would definitely return for a future visit to Stamford!"
Second floor cottage apartment located in a private community.
Beachfront cottage located in the heart of Fairfield Beach!!
On the beach
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
Terrace/patio
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
TV, fireplace, books
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
Exterior
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
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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
Fridge, microwave, oven, stovetop
Adorable 1-Bedroom Cottage in Weston, CT
10.0 out of 10, Exceptional, (30)
"Very cozy cottage a little off the beaten path in Weston. Quiet & stocked with amenities for our comfort. The owner was helpful & responsive. If there was any drawback it would be helpful to air out the cottage as its an old building & investing in some new pillows would be appreciated by the next guests. Otherwise a great stay."
The price is ￥28,051
￥43,767 total
includes taxes & fees
Sep 24 - Sep 25
Adorable 1-Bedroom Cottage in Weston, CT
Stamford Suites
Exterior
Stamford Suites
2.5 star property
6.8 out of 10, (747)
"It was more than i expected. "
The price is ￥21,899
￥25,184 total
includes taxes & fees
Oct 7 - Oct 8
Stamford Suites
DUNE Fairfield Beach
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach
3.0 star property
8.8 out of 10, Excellent, (35)
"Enjoyed the stay in the modern suite, located a short walk to the beach. Recommend the hotel and touring in the Fairfield, CT area. "
The price is ￥28,838
￥41,076 total
includes taxes & fees
Oct 1 - Oct 2
DUNE Fairfield 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.

Frequently asked questions

How much do cottages in Weston cost?
You’ll pay between ￥28,051 and ￥28,051 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 51 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.
What is there to do in Weston near my cottage?
After you’ve unpacked and settled in, set out and explore the awesome things Weston has to offer. Lucius Pond Ordway / Devil’s Den Preserve is a popular attraction to add to your must-do list.