Holiday In The Hamptons - Vacation Rentals in Westport

Sunny Westport Studio Apt. Above Historic Mill From US $204
         

10.0 (76 Reviews)
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  • Air Conditioner
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  • Pet Friendly
Sunny Westport Studio Apt. Above Historic Mill From US $390
         

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9.5 (4 Reviews)
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Delamar Westport From US $290
         

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New
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Charming 2BR Flat in Restored 1850s Cider Mill + Coworking From US $230
         

10.0 (20 Reviews)
Apartment
  • Air Conditioner
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  • Pet Friendly
Westport Gem - walk to shops, dining, town center, pet-friendly From US $391
         

Spacious Family Home From US $688
         

10.0 (1 Review)
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  • Air Conditioner
  • TV
  • Security/Safety

Luxury Places to Stay in Westport

Over 109+ Luxury Places to Stay in or Near Westport
Designer Modern Westport Estate From US $3,632
         

10.0 (4 Reviews)
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Westport Family Friendly Oasis From US $2,111
         

New
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Top-Rated Vacation Rentals with a Pool in Westport

Over 33+ Top-Rated Vacation Rentals with a Pool in or Near Westport
Westport Paradise With Every Amenity! From US $707
         

10.0 (23 Reviews)
Apartment
  • Air Conditioner
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  • Pet Friendly

Pet-Friendly Vacation Rentals in Westport

Over 34+ Pet-Friendly Vacation Rentals in or Near Westport
Cozy Westport Beachfront Retreat From US $1,022
         

New
House
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  • Pet Friendly
  • Balcony/Terrace
Stylish 2BR Apartment in Historic Cider Mill with Workspace From US $393
         

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9.5 (2 Reviews)
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Beautiful Westport Historic 4 Bedroom Gem From US $655
         

New
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Modern Farmhouse From US $887
         

10.0 (1 Review)
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Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood From US $774
         

See More Pet-Friendly Vacation Rentals in Westport on PetFriendly.io

Large Vacation Homes & Villas in Westport

Over 28+ Large Vacation Homes & Villas in or Near Westport
Amazing Water Views. Steps from Compo Beach. From US $1,116
         

10.0 (3 Reviews)
House
  • Air Conditioner
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  • TV

Wheelchair Accessible Vacation Homes in Westport

Over 5+ Wheelchair Accessible Vacation Homes in or Near Westport
Spectacular Country Home From US $757
         

New
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Vacation Ready: Beautiful House with Heated Pool From US $2,000
         

10.0 (1 Review)
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  • Parking
  • Pool

Westport Varoom and Airbnb Places to Stay Under $200

Over 4+ Westport Varoom and Airbnb Places to Stay Under $200
Historic Apartment in Downtown Westport From US $143
         

10.0 (5 Reviews)
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Inn at Longshore From US $194
         

9.2 (170 Reviews)
Hotel
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Cozy Apartment in Downtown Westport From US $146
         

New
Apartment
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Pied-à-terre in prestigious Long Lots area of Westport From US $119
         

Instantly Bookable Vacation Homes in Westport

Over 16+ Instantly Bookable Vacation Homes in or Near Westport
Designer 3BR w/Lush Yard, Gym, and Garden. From US $550
         

9.0 (2 Reviews)
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  • Air Conditioner
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Sweet Studio w/Lounge & Pool Table From US $278
         

8.8 (6 Reviews)
Apartment
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  • TV
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Walk-To-Town Cozy Colonial with Fireplace! From US $595
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pool & beach vacation in Westport, Connecticut From US $1,400
         

About Westport Vacation Rentals

With more than 118 Westport vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Holidayinthehamptons and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Westport.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Holidayinthehamptons Westport, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Westport. Places to stay near Westport are 1602.4 ft² on average, with prices averaging $1,049 a night.

Holidayinthehamptons makes it easy and safe to find and compare vacation rentals in Westport with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Westport

Type Count
Vacation Homes 91
Holiday Apartments 11
Cottages 7
Hotels with Suites 3
Villas 2
Cabin Rentals 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Westport

Pro Tip: Holidayinthehamptons makes it easy to compare the best listings on Holidayinthehamptons homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Holidayinthehamptons homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Westport.

Weather in Westport

View the weather forecast for Westport before booking your Westport Vacation Rentals to confirm your best time to go.

December - February
High 49°F       Low 25°F
March - May
High 68°F       Low 28°F
June - August
High 84°F       Low 58°F
September - November
High 78°F       Low 33°F