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

Trendy 1 bedroom +loft apartment w/ parking
Dining
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
Cozy Riverside Cottage
Exterior
Cozy Riverside Cottage
10.0 out of 10, Exceptional, (1)
"Cottage is very comfortable and clean. Neighborhood is quiet and in natural surroundings. Be prepared for spotty reception (screenshot access code) but WiFi is excellent in home, so is the TV/music system. Over all, excellent value and great accommodations in a beautiful spot. Only needed it for the weekend, but would book as a destination for some peace and quiet."
Cozy Riverside Cottage
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, (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 SAR 732
SAR 1,142 total
includes taxes & fees
24 Sep - 25 Sep
Adorable 1-Bedroom Cottage in Weston, CT
Beach house cottage steps to private beach in the heart of Bayville
Beach
Beach house cottage steps to private beach in the heart of Bayville
10.0 out of 10, Exceptional, (8)
"This is my second time here. It is so conveniently located for us being that we have family close by. I will stay here again. Thank you."
Beach house cottage steps to private beach in the heart of Bayville
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!
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
View from property
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
Private kitchen
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?
Living area
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?
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
8.0 out of 10, Very Good, (4)
"The property is in a perfect location to visit Northport on foot and has amazing views of the harbor as you are directly on the water. Main Street of Northport and the main dock and the main park with all its shops is an easy 2 minute walk from the place."
The price is SAR 713
SAR 1,021 total
includes taxes & fees
25 Sep - 26 Sep
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
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
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 SAR 938
SAR 1,691 total
includes taxes & fees
16 Oct - 17 Oct
Charming Private and Serene cottage close to I-84 and shopping
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Property grounds
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
Interior
🔥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.
9.4 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!!
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
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
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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 Westport

Westport Paradise With Every Amenity!
Guest house, and pool, as seen from the tennis court.
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, (19)
"It was fun to be able to invite our kids and grandkids over for a swim -- the owner has been extremely friendly and generous. "
The price is SAR 1,933
SAR 2,814 total
includes taxes & fees
1 Oct - 2 Oct
Westport Paradise With Every Amenity!
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill
10.0 out of 10, Exceptional, (63)
"We stayed a few nights while in the area to see a concert at Hartford Healthcare Amphitheater. Great location, very easy on/off 95, many restaurants and shops in the area too. The studio was comfortable and very clean, the bedding and towels were so nice and luxurious ! A great place to rest and recharge, lots of windows and skylights to bring the outside in. Gerard was great to work with and genuinely cared about our stay from beginning to end."
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill
Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
Enjoy the spacious lawn - an ideal retreat in this charming, quiet neighborhood.
Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
10.0 out of 10, Exceptional, (2)
"Had a great time! My favorite part was sitting on the back deck w coffee in the morning. There were so many birds and the tall hedges that protected the privacy was so charming. The host was so nice and left out fruit and snacks. Loved staying there!"
Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
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 Westport cost?
Rates for cottages in Westport range between SAR239 and SAR402 per night. No matter your budget, you’re sure to find the perfect place to touch base with nature. This price was 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 Westport?
Get in touch with nature in one of the 51 cottages on offer in Westport. To help you reserve a stay that’s right for you, make use of our handy filters to search for perks or amenities you prefer.
Why book your cottage in Westport with Expedia?
Expedia has some superb cottages in Westport, so start packing your bags for a memorable stay close to nature. If you have a budget in mind, click on how much you’d like to spend and the star rating of your property. Or, try out our filters to search for cottages with free WiFi or a pool. We’ll help you find a suitable place whatever your style of travel or plans.
How can I find cheap cottages in Westport?
With Expedia’s useful filter tool, locating cheap cottages in Westport has never been simpler. To discover properties that are friendly on the wallet, narrow your search by amenities, star rating and budget.