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 suite in Fairfield
4.92 out of 5 average rating, 109 reviewsSuite; 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
Guest suite in Fairfield
4.93 out of 5 average rating, 107 reviewsAdorable 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
Apartment in Westport
4.94 out of 5 average rating, 112 reviewsSpacious 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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Westport vacation rentals
Westport beach vacation rentals
Guest suite in Greenwich
4.91 out of 5 average rating, 423 reviewsCharming Greenwich studio, 0.2 miles from train
May 9 – 16
Apartment in Stamford
4.82 out of 5 average rating, 144 reviewsSunset Retreat: 1BR Walking Distance to the Beach
Jan 16 – 23
Home in Centerport
4.95 out of 5 average rating, 111 reviewsThe Harbor House: Beachfront Home 1 hour from NYC
Jul 24 – 31
Guest suite in Bayville
4.92 out of 5 average rating, 420 reviewsRomantic, Cozy and Private, 1 Block from Beach
Feb 22 – Mar 1
Apartment in Milford
4.97 out of 5 average rating, 505 reviewsWater front studio apartment with fireplace.
Aug 27 – Sep 3
Cottage in Riverhead
4.98 out of 5 average rating, 126 reviewsSavor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Mar 26 – Apr 2
Guest suite in Wading River
4.9 out of 5 average rating, 227 reviewsBeachy En Suite /Gateway to The North Fork
Apr 12 – 19
Apartment in Rocky Point
4.94 out of 5 average rating, 121 reviewsNorth shore Guest Room.
Jun 13 – 20
Home in Port Jefferson
4.95 out of 5 average rating, 133 reviewsThe Hidden Retreat ~ Family friendly Walk to Beach
Apr 8 – 15
Cabin in Rocky Point
4.9 out of 5 average rating, 381 reviewsGreat little place just for a couple
Nov 7 – 14
Bungalow in Milford
4.99 out of 5 average rating, 208 reviewsSpring Sale! Beach Bungalow |Walk2Beach |Pet | Pkg
Aug 11 – 18
Guest suite in Stony Brook
4.95 out of 5 average rating, 107 reviewsCozy cottage in a charming historic village!
Sep 1 – 8
Other great vacation rentals in Westport
Home in Stony Brook
4.94 out of 5 average rating, 478 reviewsSpacious Studio Apartment- near SBU
Mar 16 – 23
Home in Fairfield
4.96 out of 5 average rating, 288 reviewsLuxurious Barn With New England Charm
Nov 10 – 17
Cottage in Fairfield
4.96 out of 5 average rating, 139 reviewsCozy Home away from Home!
Dec 2 – 9
Home in Stamford
4.97 out of 5 average rating, 217 reviewsMidcentury Modern ZenHouse Sculptor Studio
May 11 – 18
Guest suite in Wilton
5.0 out of 5 average rating, 22 reviewsGuest suite with private enter
Apr 30 – May 7
Cottage in Westport
5.0 out of 5 average rating, 55 reviewsWild Rose Cottage (Westport, CT)
Sep 1 – 8
Home in Westport
5.0 out of 5 average rating, 15 reviewsCharming & Spacious New England Family Home
Dec 1 – 8
Apartment in Fairfield
5.0 out of 5 average rating, 50 reviewsBright, private 1,000 sq. ft. 1-Bedroom Apartment
Sep 29 – Oct 6
Home in Westport
5.0 out of 5 average rating, 6 reviewsFarmhouse 1899: Westport, CT
Apr 4 – 11
Guesthouse in Wilton
4.96 out of 5 average rating, 94 reviewsThe Cozy Little Cottage
May 2 – 9
Cottage in Weston
4.97 out of 5 average rating, 29 reviewsThe River Loft
Jun 27 – Jul 4
Home in Westport
5.0 out of 5 average rating, 3 reviewsWestport:Private Fire Pit Hideaway 5 min to Town
Dec 8 – 15
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.
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- Rentals with a fire pit Westport
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