Discover Your Perfect Westport Vacation Homes

Best Vacation Homes in Westport

House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 5 Guests 1200 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
£146/Night 7 Nights - £1,020
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House
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
1 Bedroom 3 Baths 8 Guests 2852.44 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
£177/Night 7 Nights - £1,238
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Hotel
Map-icon
like-icon9.8
Exceptional
(42 Reviews)
1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£278/Night 7 Nights - £1,943
Cabin
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 4 Guests 600 ft²
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£126/Night 7 Nights - £884
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House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
3 Bedrooms 3 Baths 9 Guests 2002.09 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£204/Night 7 Nights - £1,431
House
Map-icon
like-icon9.8
Exceptional
(17 Reviews)
2 Bedrooms 1 Bath 10 Guests
  • Child Friendly
    Child Friendly
£313/Night 7 Nights - £2,191
House
Map-icon
like-icon10.0
Exceptional
(32 Reviews)
3 Bedrooms 3 Baths 9 Guests 2000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£189/Night 7 Nights - £1,324
House
Map-icon
like-icon10.0
Exceptional
(18 Reviews)
3 Bedrooms 1 Bath 6 Guests 1500 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£190/Night 7 Nights - £1,329

Westport Luxury Rentals

House
Map-icon
like-icon10.0
Exceptional
(6 Reviews)
6 Bedrooms 4 Baths 14 Guests 6000 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£1,051/Night 7 Nights - £7,359
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 4 Baths 6 Guests
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£791/Night 7 Nights - £5,535
House
Map-icon
like-icon10.0
Exceptional
(7 Reviews)
3 Bedrooms 3 Baths 10 Guests 3000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£389/Night 7 Nights - £2,726
House
Map-icon
like-icon9.2
Exceptional
(48 Reviews)
3 Bedrooms 2 Baths 15 Guests 1200 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£382/Night 7 Nights - £2,674
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House
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 4 Baths 10 Guests 3003.13 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Parking
    Parking
More amenities
£378/Night 7 Nights - £2,646
House
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
3 Bedrooms 2 Baths 10 Guests
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
£349/Night 7 Nights - £2,440
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House
Map-icon
3 Bedrooms 2 Baths 15 Guests 1205.56 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
£306/Night 7 Nights - £2,143
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 1 Bath 6 Guests 1400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£284/Night 7 Nights - £1,986

Westport Pet Friendly Vacation Rentals

House
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
3 Bedrooms 1 Bath 6 Guests 1040 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£141/Night 7 Nights - £990
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House
Map-icon
like-icon9.5
Exceptional
(2 Reviews)
3 Bedrooms 1 Bath 6 Guests 1044.1 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
£175/Night 7 Nights - £1,227
House
Map-icon
like-icon9.8
Exceptional
(14 Reviews)
3 Bedrooms 2 Baths 8 Guests 2850 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£231/Night 7 Nights - £1,616
House
Map-icon
like-icon8.6
Fabulous
(6 Reviews)
2 Bedrooms 2 Baths 8 Guests
  • Pet Friendly
    Pet Friendly
  • Parking
    Parking
More amenities
£215/Night 7 Nights - £1,503
Apartment
Map-icon
like-icon9.8
Exceptional
(6 Reviews)
1 Bedroom 1 Bath 4 Guests 904 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£120/Night 7 Nights - £842
House
Map-icon
like-icon9.6
Exceptional
(38 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£144/Night 7 Nights - £1,010
Apartment
Map-icon
like-icon9.6
Exceptional
(25 Reviews)
3 Bedrooms 2 Baths 4 Guests 1000 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
More amenities
£119/Night 7 Nights - £836
House
Map-icon
like-icon9.6
Exceptional
(4 Reviews)
3 Bedrooms 2 Baths 8 Guests 1399 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£141/Night 7 Nights - £988

Westport Large Vacation Homes

House
Map-icon
5 Bedrooms 4 Baths 15 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£570/Night 7 Nights - £3,991
Cabin
Map-icon
like-icon10.0
Exceptional
(31 Reviews)
3 Bedrooms 2 Baths 11 Guests 4000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£295/Night 7 Nights - £2,067
House
Map-icon
5 Bedrooms 2 Baths 20 Guests 1550 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
£404/Night 7 Nights - £2,830

Why Choose Rent By Owner for your Westport Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Westport

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this destination in Indiana can significantly enhance your experience, so consider the seasonal weather patterns and local events to find the ideal period for booking your vacation rentals here.

Peak Season Highlights

summer
Late Spring to Early Summer (May - June)

During this period, the region experiences warm weather ideal for outdoor activities and exploring local sights. It’s a popular time to visit if you want pleasant temperatures and lively community events.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September - October)

The early fall months offer mild weather and vibrant foliage, making it a favored season for enjoying the area's scenic beauty and outdoor adventures. This is also when the region sees increased visitor interest.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December - February)

With cooler temperatures and fewer tourists, winter provides a quieter experience in the area. It’s an ideal time for those seeking solitude and cozy stays in comfortable vacation rentals.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
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Early Spring (March - April)

As the region transitions into warmer weather, early spring offers a peaceful atmosphere with less crowding. This period is perfect for enjoying the natural surroundings in a more relaxed setting.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Westport

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining with a private barbecue grill, perfect for summer evenings in the area.
  • Relax on a spacious patio or deck that offers scenic views of the surrounding countryside.
  • Take advantage of lush lawns and open spaces ideal for outdoor games and activities.
  • Make use of a fire pit area to gather with family and friends during cool evenings.
  • Benefit from access to nearby hiking trails or nature paths for outdoor exploration.
  • Utilize a boat dock or access point if your stay includes water-based recreation on local lakes or rivers.
  • Enjoy swimming or lounging by an outdoor pool, often available in well-equipped properties close to this region.
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Family Activities

  • Westport Park: Enjoy a family picnic or a leisurely walk in this scenic park nestled within the area, perfect for outdoor activities with kids.
  • Hoosier Heritage Museum: Explore local history through engaging exhibits that offer an educational experience for the entire family visiting here.
  • Southern Indiana Adventure Zone: Experience fun-filled days with interactive play areas and activities designed to keep children entertained in this regional destination.
  • Indian Creek Park: Spend quality time by the water, where you can engage in fishing, kayaking, or simply relaxing amidst the natural surroundings of the area.
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Adult Activities

  • Sailing and Boating on the White River: Enjoy a relaxing day on the water by renting a boat or joining a guided cruise along the White River, immersing yourself in the scenic beauty of the region.
  • Hiking at the Hoosier National Forest: Explore miles of trails through lush forests and rolling hills that provide an ideal setting for outdoor adventures near your vacation rental.
  • Cast your line in local lakes and rivers, which are renowned for their fishing opportunities that attract anglers from across the region.
  • Play a round of golf at nearby courses that offer picturesque fairways and a peaceful atmosphere just minutes from your stay here.

Westport Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Outdoor Adventures: Take advantage of the area's scenic natural landscapes by scheduling outdoor activities early to enjoy the best weather and avoid peak crowds.
  • Explore Local Dining Options: Discover the region's unique culinary scene by trying nearby eateries that highlight local flavors during your stay.
  • Choose a Strategic Location: Select vacation rentals close to key attractions or amenities to maximize your time exploring and minimize travel within this charming destination.
  • Check for Seasonal Events: Stay informed about local events or festivals happening during your visit to experience the area's culture and community firsthand.

Transportation Options

  • Westport Transit Service: This local bus service offers convenient transportation throughout the area, making it easy to explore nearby attractions from your vacation rental.
  • Rental Car Services: Several major rental car companies operate here, providing the flexibility to discover the region at your own pace and convenience.
  • Taxi and Rideshare Options: Taxis and rideshare services like Uber and Lyft are readily available, offering quick and reliable transportation within the destination.
  • Private Shuttle Services: Private shuttle options are accessible for travelers seeking a comfortable and direct way to reach popular destinations in the region.

Local Customs Options

  • Traditional Hoosier Hospitality: You can expect friendly interactions and warm welcomes from locals who take pride in sharing their Southern Indiana roots.
  • Celebration of Local Heritage: Participating in or observing regional festivals and events offers a glimpse into the area's rich history and community spirit.
  • Respect for Nature and Land: Outdoor customs here emphasize conservation and appreciation for the scenic landscapes surrounding the destination.
  • Community Gatherings and Farmers Markets: Engaging with local markets provides an authentic experience of regional produce and craftsmanship that define this region.

Frequently Asked Questions About Westport?

2. Which vacation homes in Westport are best for families?

If you are looking for a family-friendly vacation home in Westport, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Westport:

3. How many Rentbyowner vacation rentals are available in Westport?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 73 in the Westport area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Westport. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by listing, so you should review the specific property's terms before booking. Most owners provide detailed cancellation information in the listing or contact them directly for clarification.

5. How do I know if a vacation rental in the region is available on my travel dates?

Availability is displayed on each listing. To confirm your preferred dates, simply check the calendar or send an inquiry to the property owner for real-time availability updates.

6. Are there any additional fees associated with booking a vacation rental here?

Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing details. Always review the total price before completing your reservation to understand all costs involved.

7. What amenities can I expect from vacation rentals in this destination?

Most properties offer amenities like Wi-Fi, parking, and kitchen facilities. Specific features are listed on each property’s page, so check the listing details to ensure it meets your needs.

8. How do I contact the owner if I have special requests or questions about my stay?

You can reach out to the property owner directly through the contact option provided on the listing. Owners are usually responsive and happy to assist with any special arrangements or inquiries.

Westport Top Rated Vacation Rentals

Hotel
Map-icon
like-icon9.2
Exceptional
(66 Reviews)
12 Baths 32.29 ft²
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
£132/Night 7 Nights - £921
Hotel
Map-icon
like-icon9.0
Exceptional
(350 Reviews)
1 Bath
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£122/Night 7 Nights - £851
Hotel
Map-icon
like-icon8.6
Fabulous
(647 Reviews)
1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£115/Night 7 Nights - £807
star-icons-3
Hotel
Map-icon
like-icon7.4
Very Good
(67 Reviews)
1 Bath 390.19 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£144/Night 7 Nights - £1,005
Hotel
Map-icon
like-icon7.4
Very Good
(18 Reviews)
1 Bath
  • Pool
    Pool
  • Breakfast
    Breakfast
More amenities
£78/Night 7 Nights - £548
star-icons-5
Hotel
Map-icon
like-icon7.1
Very Good
(49 Reviews)
3 Baths 215.28 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£76/Night 7 Nights - £532