Holiday houses in Westport

4.92 out of 5 average rating, 150 reviews

Guest suite in Fairfield

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; exclusive use of kitchen (was the main kitchen of the house); private entrance to space thru side door of the house. Two 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.

5 out of 5 average rating, 33 reviews

Farmhouse 1899: Minutes to Downtown Westport, CT

Welcome to Farmhouse 1899. This old house is full of charm and history and is the perfect mix of old and new. Every inch of this home has been meticulously designed and furnished by a NYC real estate professional intent on recreating a 19th century farmhouse vibe for today’s modern family. Enjoy easy access to everything from this centrally located home. Close to 2 major highways, a 10 minute walk or 3 minute drive to Downtown Westport where you can enjoy great shops, restaurants and nightlife.

4.9 out of 5 average rating, 232 reviews

Apartment in Westport

Spacious Westport Apt surrounded by nature!

Spacious mother-in-law basement apartment with private entrance that opens to the backyard. Large 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 for up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, hikes, wonderful bakeries and restaurants.

5 out of 5 average rating, 21 reviews

Guesthouse in Norwalk

Waterfront Getaway - Norwalk, CT

Enjoy a stylish experience at this prime location - ideal to explore, relax, or WFH. This beautiful seaside home has full direct waterfront views of the Norwalk Harbor and LI Sound from every room and a balcony. NYC is a quick ride away, with a train station just 0.4 miles away. Across the street is our lovely Veteran's Memorial Park with a route going to Calf Pasture Beach! Experience fine dining in SoNO, long lines at Mr. Frosty's Ice Cream, and more. You won't want to miss this experience.

4.97 out of 5 average rating, 124 reviews

Guesthouse in Wilton

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed and the living room has a futon couch which folds down. It’s perfect for 1-2 adults, can comfortably fit 3 people if one is a child.

4.97 out of 5 average rating, 143 reviews

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

5 out of 5 average rating, 55 reviews

Westport Deco HAUS /5 min to Town /10 min to Beach

Welcome to the enchanting home of the late Jean Woodham, a celebrated sculptor renowned for her abstract and expressive works. This unique property, nestled in a serene neighborhood in Westport, harmonizes artistic charm with modern comforts, promising a distinct experience for guests seeking inspiration and relaxation. Upon entering, you're welcomed by an inviting atmosphere that mirrors Woodham's creative spirit. The space feels spacious and open, with an eclectic mix of artwork.

4.91 out of 5 average rating, 152 reviews

Guest suite in Norwalk

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.

4.98 out of 5 average rating, 136 reviews

Apartment in Norwalk

"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 .

5 out of 5 average rating, 35 reviews

Guest suite in Norwalk

Cozy 1 Bd Private Entrance In-law Suite & Hot Tub

Charming Getaway in Norwalk, CT - Discover comfort and convenience in this cozy low ceiling short-term rental located just 5 minutes from local markets, dining spots, Norwalk River Valley Trail, Norwalk Hospital and shopping centers. Perfect for single travelers, work related or weekend adventurers, this space offers a warm, inviting atmosphere with modern amenities. Enjoy easy access to local attractions and scenic spots, the perfect base for exploring coastal Connecticut!

4.82 out of 5 average rating, 180 reviews

Guest suite in Wilton

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.

Place to stay in Southport

4.96 out of 5 average rating, 319 reviews

Sunny Westport 2 BR Retreat above Historic Mill

Historic Cider Mill Retreat – A Unique Stay for Leisure & Business Travelers Experience the charm of history blended seamlessly with modern comfort in this eclectic, sun-filled apartment perched atop a beautifully restored 1850s cider mill. Thoughtfully designed and furnished by our team of artisans, this unique getaway offers panoramic views, breathtaking surroundings, and a rich historical ambiance that makes for a truly unforgettable stay.

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Popular amenities for Westport holiday rentals

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Stay near Westport's top sights

Compo Beach12 locals recommend

Sherwood Island State Park10 locals recommend

Calf Pasture Beach16 locals recommend

Other great holiday rentals in Westport

4.85 out of 5 average rating, 72 reviews

Apartment in Southport

Zen studio in Historic Southport Village.

ReneeRating, 5 stars1 week ago

We loved staying at Kellie’s studio. It’s the best location in our favorite town.

5 out of 5 average rating, 3 reviews

Westport In-Town Retreat

HannahRating, 5 stars1 month ago

Such a great stay to enjoy the best of Westport and surrounding area! Amazing location. The house is well appointed with plenty of spaces for guests to enjoy (multiple living areas, huge outdoor patio, dine-in kitchen).

5 out of 5 average rating, 59 reviews

Cottage in Westport

Mill Pond Retreat

JenniferRating, 5 stars10 months ago

Laurajean was an incredibly warm, accomodating, and responsive host. Her home is lovely and in an incredibly peaceful spot in Westport, we loved our time there!

Private room in Fairfield

4.98 out of 5 average rating, 153 reviews

LOVELY WELL APPOINTED ROOM - IN FAIRFIELD

JorgeRating, 5 stars1 week ago

Everything you can ask for and feel that you only get at home. Even when I had to extend my stay they made it very easy to make the change and welcomed me warmly. THANKS FOR EVERYTHING!!

5 out of 5 average rating, 15 reviews

Home in Fairfield

Stareway to Heaven

FernandoRating, 5 stars1 month ago

We were visiting Fairfield for our youngest son's graduation. We are a big family, all adult children. The house was everything we had hoped for - a beautiful, roomy, easy to use kitchen with a big dining table where we could enjoy each other's company. Rooms and beds for all that were so comfortable. The scenery this time of the year was amazing. As a big family, having a place to meet and spend time together is of utmost importance for us and we were able to accomplish this during our stay. Thank you!

Home in Philipstown

5 out of 5 average rating, 9 reviews

Arkadia House Mid-century retreat with pool & view

AriRating, 5 stars71 months ago

Dan and Andrew were great hosts and very easy to communicate with. The location was beautiful and the views were amazing. The house was stocked with everything you could possibly need; towels, bedsheets, blankets cookware, a bunch of basic food necessities & more. The pool was refreshing after laying in the sun and watching the sunset from the pool is truly a must when visiting this home. We would love to stay here again and highly recommend to others looking for a gorgeous getaway home.

4.92 out of 5 average rating, 24 reviews

Beautiful Brand New Inviting Farmhouse

AlexaRating, 5 stars7 months ago

My bridesmaids and I booked with Sean for our wedding weekend and it was perfect! The check in process and house instructions were so clear and easily accessible— perfect to not have to worry about it right before my wedding! The house is beautiful and we got ready the morning of the wedding there and it could not have been more perfect! Definitely recommend!