Holiday houses in Westport

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Top-rated holiday rentals in Westport

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Guest favourite

Guest suite in Fairfield

4.92 out of 5 average rating, 119 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

Guest favourite

Guest suite in Fairfield

4.93 out of 5 average rating, 115 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

Guest favourite

Guest suite in Wilton

4.9 out of 5 average rating, 106 reviews

Serene Pond Views charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Guest favourite

Apartment in Westport

4.92 out of 5 average rating, 126 reviews

Spacious Westport Apt surrounded by nature

Spacious mother-in-law apartment w/ private entrance on the 1st floor of our beautiful home. Windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8-10 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, and wonderful bakeries and restaurants nearby!

Guest favourite

Guesthouse in Norwalk

4.97 out of 5 average rating, 214 reviews

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

Guest favourite

Home in Westport

4.89 out of 5 average rating, 46 reviews

Westport/Saugatuck super spot

Arrive by car, train or kayak. Great place to stay if you want a place close to everything Westport has to offer. Spacious 1 bedroom, large living room w/ queen sleeper sofa. Everything new (furniture, decor, linens, kitchen gear) as of Jan '23. No smoking or animals…please do not ask for an exception. Note: The Riverside unit on lower level w/ 2 bedrooms is also available to rent for larger groups of 5-8. This unit is on upper level so guests must be comfortable with stairs.

Guest favourite

Guesthouse in Norwalk

5.0 out of 5 average rating, 118 reviews

Private one bedroom cottage on Conn. seashore

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian friendly town; you don't even need a car while here.

Guest favourite

Guest suite in Norwalk

4.9 out of 5 average rating, 112 reviews

Efficiency Garden Studio in South Norwalk, CT

Beautiful Efficiency Studio with private entrance in South Norwalk. Self-contained with private bath, kitchenette and off street parking. 10 min walk to South Norwalk Rail Station. 60 minutes to Manhattan, 10 min to historic SoNo. 10 min drive to Stamford. 5 minute drive to Merritt 7 and corporate business district. 5 minute to Norwalk Hospital. 5 min to City Hall. Close to all main arteries. Part of a quaint and charming arts & crafts bungalow, has separate entrance, very quiet.

Guest favourite

Apartment in Norwalk

4.97 out of 5 average rating, 101 reviews

"Triplex Historic Beauty" with Seasonal Garden

Featured on the History Channel hit TV series "American Pickers"! Come join us at the head of the harbor in historic downtown Norwalk "Wall Street" neighborhood. This cozy second floor rental has been tastefully decorated with new and old. In addition to the photo descriptions we have included a floor plan for review. Please note the neighborhood is a working waterfront during the day and the Danbury active train line runs behind the building which adds to the character .

Guest favourite

Apartment in Brookfield

4.94 out of 5 average rating, 189 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Guest favourite

Guest suite in Wilton

4.94 out of 5 average rating, 51 reviews

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Guest favourite

Place to stay in Westport

4.94 out of 5 average rating, 235 reviews

Sunny Westport Studio Apt. Above Historic Mill

This sunny studio apartment, atop a renovated historic Mill, is charming and unique. With panoramic views and breathtaking surroundings, including endless flora and fauna, and a contingent of mallards, egrets, and swans, this hideaway may be moments from Southport Village, but feels like many miles from everything. Original hardwood floors and updated amenities make for a charming place to rest your bones, if only for the evening.