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.

Guest favorite

Guest suite in Fairfield

4.92 out of 5 average rating, 109 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.

Oct 24 – 31

€ 126 per night
Guest favorite

Guest suite in Fairfield

4.93 out of 5 average rating, 107 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.

Aug 18 – 25

€ 140 per night
Guest favorite

Apartment in Westport

4.94 out of 5 average rating, 112 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 6 – 13

€ 185 per night

Popular amenities for Westport vacation rentals

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

Westport beach vacation rentals

Superhost

Guest suite in Greenwich

4.91 out of 5 average rating, 423 reviews

Charming Greenwich studio, 0.2 miles from train

May 9 – 16

€ 143 per night
Superhost

Apartment in Stamford

4.82 out of 5 average rating, 144 reviews

Sunset Retreat: 1BR Walking Distance to the Beach

Jan 16 – 23

€ 140 per night
Guest favorite

Home in Centerport

4.95 out of 5 average rating, 111 reviews

The Harbor House: Beachfront Home 1 hour from NYC

Jul 24 – 31

€ 732 per night
Guest favorite

Guest suite in Bayville

4.92 out of 5 average rating, 420 reviews

Romantic, Cozy and Private, 1 Block from Beach

Feb 22 – Mar 1

€ 83 per night
Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 505 reviews

Water front studio apartment with fireplace.

Aug 27 – Sep 3

€ 219 per night
Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Mar 26 – Apr 2

€ 708 per night
Guest favorite

Guest suite in Wading River

4.9 out of 5 average rating, 227 reviews

Beachy En Suite /Gateway to The North Fork

Apr 12 – 19

€ 93 per night
Guest favorite

Apartment in Rocky Point

4.94 out of 5 average rating, 121 reviews

North shore Guest Room.

Jun 13 – 20

€ 94 per night
Superhost

Home in Port Jefferson

4.95 out of 5 average rating, 133 reviews

The Hidden Retreat ~ Family friendly Walk to Beach

Apr 8 – 15

€ 439 per night
Guest favorite

Cabin in Rocky Point

4.9 out of 5 average rating, 381 reviews

Great little place just for a couple

Nov 7 – 14

€ 152 per night
Guest favorite

Bungalow in Milford

4.99 out of 5 average rating, 208 reviews

Spring Sale! Beach Bungalow |Walk2Beach |Pet | Pkg

Aug 11 – 18

€ 344 per night
Guest favorite

Guest suite in Stony Brook

4.95 out of 5 average rating, 107 reviews

Cozy cottage in a charming historic village!

Sep 1 – 8

€ 178 per night

Other great vacation rentals in Westport

Guest favorite

Home in Stony Brook

4.94 out of 5 average rating, 478 reviews

Spacious Studio Apartment- near SBU

Mar 16 – 23

€ 101 per night
Guest favorite

Home in Fairfield

4.96 out of 5 average rating, 288 reviews

Luxurious Barn With New England Charm

Nov 10 – 17

€ 270 per night
Guest favorite

Cottage in Fairfield

4.96 out of 5 average rating, 139 reviews

Cozy Home away from Home!

Dec 2 – 9

€ 367 per night
Guest favorite

Home in Stamford

4.97 out of 5 average rating, 217 reviews

Midcentury Modern ZenHouse Sculptor Studio

May 11 – 18

€ 390 per night
Guest favorite

Guest suite in Wilton

5.0 out of 5 average rating, 22 reviews

Guest suite with private enter

Apr 30 – May 7

€ 99 per night
Guest favorite

Cottage in Westport

5.0 out of 5 average rating, 55 reviews

Wild Rose Cottage (Westport, CT)

Sep 1 – 8

€ 371 per night
Guest favorite

Home in Westport

5.0 out of 5 average rating, 15 reviews

Charming & Spacious New England Family Home

Dec 1 – 8

€ 503 per night
Guest favorite

Apartment in Fairfield

5.0 out of 5 average rating, 50 reviews

Bright, private 1,000 sq. ft. 1-Bedroom Apartment

Sep 29 – Oct 6

€ 164 per night
Guest favorite

Home in Westport

5.0 out of 5 average rating, 6 reviews

Farmhouse 1899: Westport, CT

Apr 4 – 11

€ 758 per night
Guest favorite

Guesthouse in Wilton

4.96 out of 5 average rating, 94 reviews

The Cozy Little Cottage

May 2 – 9

€ 162 per night
Guest favorite

Cottage in Weston

4.97 out of 5 average rating, 29 reviews

The River Loft

Jun 27 – Jul 4

€ 401 per night
Superhost

Home in Westport

5.0 out of 5 average rating, 3 reviews

Westport:Private Fire Pit Hideaway 5 min to Town

Dec 8 – 15

€ 505 per night

Quick stats about vacation rentals in Westport

Total rentals

120 properties

Rentals with dedicated workspaces

70 properties have a dedicated workspace

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

90 properties are a good fit for families

Total number of reviews

2.2K 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 160 vacation rentals in Greenfield Hill, over 110 vacation rentals in Greens Farms, and over 220 vacation rentals in Saugatuck.

  • Are there vacation rentals with a dedicated workspace in Westport?

    Yes! Work meets play with ease at over 70 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 50 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 20 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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Fairfield County
  5. Westport