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Compare 49 Cottages in Westport with updated reviews, rates, and availability.

Cozy Cabin @ Sticks & Stones Farm

Cozy Cabin @ Sticks & Stones Farm

8.0 out of 10, Very Good, (1)
"This property was just what we needed when visiting the area. The rustic but peaceful setting is one we wish we could have enjoyed more of. We would have loved to have spent more time on property with a fire in the wood stove or relaxing by the brook out back. The mattresses were comfortable and we slept well. "
The price is SAR 533
SAR 913 total
includes taxes & fees
19 Jan - 20 January 2025
Cozy Cabin @ Sticks & Stones Farm
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
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
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, (9)
"Great location. Very clean modern cottage by the sea. Would love to stay again. "
Beach house cottage steps to private beach in the heart of Bayville
🔥Fairfield County Cozy cottage , super close great adventure
Living area

🔥Fairfield County Cozy cottage , super close great adventure

9.8 out of 10, Exceptional, (7)
"Clean property, quiet neighborhood, great location. Close to Sacred Heart Univ."
🔥Fairfield County Cozy cottage , super close great adventure
Trendy 1 bedroom +loft apartment w/ parking
Interior

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (5)
"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
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!
Wow Waterfront Sunset Oasis Beach Cottage Village Winery Brewery East End NYC Hr
Miscellaneous

Wow Waterfront Sunset Oasis Beach Cottage Village Winery Brewery East End NYC Hr

8.8 out of 10, Excellent, (6)
"Very cute cottage on the water with a deck and beautiful views. A short walk into town to shops and restaurants. "
Wow Waterfront Sunset Oasis Beach Cottage Village Winery Brewery East End NYC Hr
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, (34)
"beautiful cottage with all the amenities you need.. charming historic property.. would highly recommend "
The price is SAR 733
SAR 1,128 total
includes taxes & fees
30 Dec - 31 Dec
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, (3)
"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
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!
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
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!
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
Ridgefield Cottage: Walk to Town & Movie Theater!
Ridgefield Vacation Rental | 1BR | 1BA | 675 Sq Ft | Step-Free Access

Ridgefield Cottage: Walk to Town & Movie Theater!

Ridgefield Cottage: Walk to Town & Movie Theater!
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, (23)
"We had such a nice stay at Mark and Sarah’s. Check in was so easy and they were very attentive to anything we needed. The property and apartment are beautiful, it was so nice waking up and seeing all the trees and it was so quiet. We will definitely be back and stay when we are visiting our daughter at Fairfield."
The price is SAR 1,841
SAR 2,653 total
includes taxes & fees
24 Dec - 25 Dec
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, (68)
"Can’t say enough good things about studio apartment! Gerard was wonderful and easy to communicate with. This apartment had absolutely everything we needed! The airline lost one of our bags, so the onsite washing machine was very much appreciated! We will definitely be back to stay here again!"
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Enjoy the spacious lawn - an ideal retreat in this charming, quiet neighborhood.

Stay 3 Nights or Longer Until January 31 and Get 15% Off

10.0 out of 10, Exceptional, (3)
"After a rough year we were able to get a few days away and at the last minute chose this location. Everything we were looking for was there. The home and grounds were beautiful. The location in Westport was exactly what we wanted: magnificent fall foliage, quiet where the home was but close enough to walk to town and enjoy every aspect of being close by the town for lovely cafes and restaurants. Also, beautiful places were accessible by car in minutes such as Earthplace for trails and nature...
Stay 3 Nights or Longer Until January 31 and Get 15% Off
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?
You can expect to pay between SAR 533 and SAR 733 per night for cottages in Westport. No matter your budget, an ideal stay is only 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 Westport?
Lock in your vacation dates and then pick from 49 cottages in Westport. Thinking about a place where you can get reacquainted with nature? Expedia will help you find your ideal escape in a few simple clicks.
Why book your cottage in Westport with Expedia?
We think that a vacay should be stress-free, so if you’re after cottages in Westport at an affordable price, Expedia has you covered. Save cash and stay in an inexpensive option far away from the city rush, or book a luxury cottage to really spoil your favorite people.
How can I find cheap cottages in Westport?
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