Westport vacation rentals

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Top-rated vacation rentals in Westport

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Fairfield

4.92 out of 5 average rating, 111 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.

Feb 7 – 14

R2,267 ZAR per night

Guest favorite

Guest suite in Fairfield

4.93 out of 5 average rating, 110 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.

Nov 21 – 28

R2,183 ZAR per night

Guest favorite

Guest suite in Wilton

4.9 out of 5 average rating, 103 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…

Aug 5 – 12

R2,686 ZAR per night

Guest favorite

Apartment in Westport

4.93 out of 5 average rating, 116 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!

Jan 7 – 14

R3,396 ZAR per night

Guest favorite

Guesthouse in Norwalk

4.99 out of 5 average rating, 208 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.

Aug 23 – 30

R2,239 ZAR per night

Guest favorite

Home in Milford

4.98 out of 5 average rating, 153 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Dec 20 – 27

R8,380 ZAR per night

Guest favorite

Guesthouse in Norwalk

5.0 out of 5 average rating, 113 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.

Jul 11 – 16

R6,506 ZAR per night

Guest favorite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

May 3 – 10

R2,404 ZAR per night

Guest favorite

Place to stay in Westport

4.95 out of 5 average rating, 229 reviews

Sunny Westport Studio Apt. Above Historic Mill

No ugly duckling. Fall asleep to the sounds of a centurys-old waterfall in this sunny studio apartment, atop a renovated historic Mill. 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.

Oct 24 – 31

R3,339 ZAR per night

Guest favorite

Guest suite in Norwalk

4.9 out of 5 average rating, 111 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.

Jan 19 – 26

R1,755 ZAR per night

Guest favorite

Apartment in Redding

4.94 out of 5 average rating, 459 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your spring getaway to the Huckleberry Quarters, a totally renovated (2015) studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A Perfect weekend getaway or writing/artist space. Easy access to Merritt Parkway, trains, local eateries, parks.

Mar 13 – 20

R2,743 ZAR per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 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.

Feb 9 – 16

R2,414 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Westport vacation rentals

Laptop-friendly workspace

Stay near Westport's top sights

Whole Foods Market22 locals recommend

Trader Joe's62 locals recommend

bartaco71 locals recommend

Shake Shack6 locals recommend

Black Duck Cafe13 locals recommend

Bow Tie Cinema Royale 66 locals recommend

Other great vacation rentals in Westport

Guest favorite

Apartment in Northport

4.91 out of 5 average rating, 130 reviews

Harbor Studio - Across from historic Northport doc

Jan 13 – 20

R2,447 ZAR per night

Guest favorite

Guest suite in Bayville

4.91 out of 5 average rating, 426 reviews

Romantic, Cozy and Private, 1 Block from Beach

Dec 4 – 11

R1,631 ZAR per night

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 509 reviews

Water front studio apartment with fireplace.

Sep 26 – Oct 3

R3,855 ZAR per night

Guest favorite

Cottage in Milford

4.96 out of 5 average rating, 235 reviews

Spring Sale! Cozy Cottage | Pet | Walk to Beach

Nov 3 – 10

R3,631 ZAR per night

Superhost

Apartment in Stamford

4.82 out of 5 average rating, 146 reviews

Sunset Retreat: 1BR Walking Distance to the Beach

Feb 22 – Mar 1

R2,520 ZAR per night

Guest favorite

Home in Centerport

4.96 out of 5 average rating, 112 reviews

The Harbor House: Beachfront Home 1 hour from NYC

Aug 19 – 26

R14,902 ZAR per night

Guest favorite

Apartment in Mamaroneck

4.93 out of 5 average rating, 176 reviews

2 Bed/1 Bath Private Apartment in Mamaroneck

Jan 13 – 20

R2,651 ZAR per night

Guest favorite

Guest suite in Wading River

4.9 out of 5 average rating, 230 reviews

Beachy En Suite /Gateway to The North Fork

Oct 6 – 13

R2,234 ZAR per night

Show all

Other great vacation rentals in Westport

Guest favorite

Home in Wilton

4.93 out of 5 average rating, 160 reviews

Mid Century Modern Cottage

Jul 23 – 30

R3,096 ZAR per night

Guest favorite

Apartment in Deer Park

4.97 out of 5 average rating, 112 reviews

Best Studio-Private Entrance+Parking-Close To All

Feb 6 – 13

R2,204 ZAR per night

Guest favorite

Guest suite in Stamford

4.93 out of 5 average rating, 111 reviews

Charming Retreat in North Stamford

Mar 10 – 17

R1,701 ZAR per night

Guest favorite

Home in Fairfield

4.96 out of 5 average rating, 289 reviews

Luxurious Barn With New England Charm

Apr 14 – 21

R4,547 ZAR per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 109 reviews

Sunny Lakeview Guesthouse

Nov 26 – Dec 3

R2,384 ZAR per night

Guest favorite

Home in Stamford

4.97 out of 5 average rating, 219 reviews

Midcentury Modern ZenHouse Sculptor Studio

Nov 30 – Dec 7

R7,390 ZAR per night

Guest favorite

Apartment in Stamford

4.97 out of 5 average rating, 122 reviews

Sugar Shack Studio | Downtown Skyline Views

Feb 21 – 28

R2,688 ZAR per night

Guest favorite

Guest suite in Wilton

4.95 out of 5 average rating, 39 reviews

Guest suite with private enter

Jul 28 – Aug 4

R1,872 ZAR per night

Show all

Quick stats about vacation rentals in Westport

Total rentals
120 properties
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
2.3K reviews

Frequently Asked Questions

Where should I stay in Westport?
Make yourself at home in Westport by choosing from our most frequently booked neighborhoods. We have over 110 vacation rentals in Greens Farms, over 220 vacation rentals in Saugatuck, and over 160 vacation rentals in Greenfield Hill.
Are there vacation rentals with a dedicated workspace in Westport?
Yes! Work meets play with ease at over 80 vacation rentals in Westport featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Westport?
Four-legged friends are welcome in Westport. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there Westport vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Westport, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Westport have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Westport. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westport have a gym?
Absolutely! We offer over 20 house rentals with a gym in Westport. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westport have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Westport. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Westport?
Westport has more than 80 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Westport vacation rentals

Top-rated vacation rentals in Westport

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Westport vacation rentals

Stay near Westport's top sights

Other great vacation rentals in Westport

Apartment in Northport

Guest suite in Bayville

Apartment in Milford

Cottage in Milford

Apartment in Stamford

Home in Centerport

Apartment in Mamaroneck

Guest suite in Wading River

Other great vacation rentals in Westport

Home in Wilton

Apartment in Deer Park

Guest suite in Stamford

Home in Fairfield

Guesthouse in Mahopac

Home in Stamford

Apartment in Stamford

Guest suite in Wilton

Quick stats about vacation rentals in Westport

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Westport?

Are there vacation rentals with a dedicated workspace in Westport?

Are there pet-friendly vacation rentals in Westport?

Are there Westport vacation rentals on Airbnb with pools?

Do house rentals in Westport have a bbq area?

Do house rentals in Westport have a gym?

Do house rentals in Westport have self check-in?

Are there family-friendly house rentals in Westport?

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