Compare Westport Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Westport Rentals

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

3.5 out of 5
93 East Avenue, Norwalk, CT
Free Cancellation
Reserve now, pay when you stay
3.09 mi from city center
$279 nightly
The price is $321 total per night
$321 total
Oct 5 - Oct 6
Total with taxes and fees
Guesthouse at Norwalk Inn features a gym, free WiFi in public areas, and a conference center. There's free parking, and a shuttle from the hotel to the airport (available 24 hours) for USD 150 per room. The front desk is staffed 24/7 to help with tours or tickets, luggage storage, and securing valuables. Other amenities at this historic aparthotel include a 24-hour business center, a seasonal outdoor pool, and a computer station.
DUNE Fairfield Beach

DUNE Fairfield Beach

3 out of 5
1160 Reef Rd, Fairfield, CT
5.99 mi from city center
$252 nightly
The price is $290 total per night
$290 total
Oct 21 - Oct 22
Total with taxes and fees
DUNE Fairfield Beach features free WiFi in public areas, spa treatment rooms, and free use of bicycles. A stay here includes free parking. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this beach apartment building include express check-in, express check-out, and wedding services.
price will make you book twice , luxury living

price will make you book twice , luxury living

Norwalk, CT
4.78 mi from city center
$146 nightly
The price is $165 total per night
$165 total
Sep 30 - Oct 1
Total with taxes and fees
At this apartment, guests have access to laundry facilities, local meal delivery service, and a living plant wall. Additional amenities include barbecue grills and a garden.
Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.

8.78 mi from city center
$393 nightly
The price is $446 total per night
$446 total
Sep 30 - Oct 1
Total with taxes and fees
At this apartment, guests have access to features like an arcade/game room. This family-friendly apartment building also has barbecue grills.
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

9.1 mi from city center
$1,190 nightly
The price is $1,351 total per night
$1,351 total
Sep 30 - Oct 1
Total with taxes and fees
Guests of this vacation home enjoy free WiFi in public areas, a terrace, and laundry facilities. Free parking is included with your stay. Additional amenities include a picnic area and a garden.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
40 Beechmont Ave, Bridgeport, CT
9.1 mi from city center
$827 nightly
The price is $951 total per night
$951 total
Sep 30 - Oct 1
Total with taxes and fees
Guests of Beechmont - Perfect for Family Retreat! enjoy access to free WiFi in public areas, microwave in a common area, and refrigerator in a common area. You can take advantage of free parking if you drive. Friendly staff can provide luggage storage, and also offer advice about sightseeing. Other amenities at this luxury vacation home include a terrace, laundry facilities, and a TV in a common area.
Business or Weekend escape

Business or Weekend escape

11.34 mi from city center
$130 nightly
The price is $147 total per night
$147 total
Sep 30 - Oct 1
Total with taxes and fees
At this vacation home, guests have access to barbecue grills.
Stamford Suites

Stamford Suites

4 out of 5
720 Bedford St, Stamford, CT
Free Cancellation
Reserve now, pay when you stay
10.9 mi from city center
$132 nightly
The price is $152 total per night
$152 total
Oct 5 - Oct 6
Total with taxes and fees
At Stamford Suites, guests have access to free WiFi in public areas, express check-in, and express check-out. There's free parking if you drive. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, luggage storage, and concierge services. Additional amenities include free newspapers, laundry facilities, and a vending machine.
Luxury Apartments by Hyatus at The Asher

Luxury Apartments by Hyatus at The Asher

4.5 out of 5
150 Broad St, Stamford, CT
11.03 mi from city center
Guests staying at Luxury Apartments by Hyatus at The Asher enjoy a gym, a rooftop terrace, and free WiFi in public areas. Free parking is included with your stay. A multilingual staff is on hand to assist with concierge services and access to locker space. Other amenities at this luxury aparthotel include meeting rooms, a seasonal outdoor pool, and laundry facilities.
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

13.47 mi from city center
$176 nightly
The price is $199 total per night
$199 total
Oct 6 - Oct 7
Total with taxes and fees
At this vacation home, guests have access to a garden.
Kitchen
Free WiFi
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

16.87 mi from city center
Guests staying at this cottage enjoy a water park, barbecue grills, and a garden.
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow

Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow

16.87 mi from city center
$829 nightly
The price is $947 total per night
$947 total
Sep 30 - Oct 1
Total with taxes and fees
Guests staying at this vacation home enjoy a water park, a hot tub, and laundry facilities. Other amenities at this beach vacation home include local meal delivery service, a water dispenser, and barbecue grills.
Don't see what you're looking for?
See all available properties in Westport
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Westport Large Group Rentals

How to Book Vacation Rentals in Westport



🏠 What is the best price for Westport vacation rentals?

Westport vacation rentals range in price, starting at $147 per night.


🏠 What types of vacation rentals in Westport can I rent?

Orbitz offers a wide range of Westport rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Westport condo rentals.


🏠 Is it free to cancel my Westport vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Westport vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Westport. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Westport?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Westport apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Westport?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Westport package deals will get you even more savings.

More to Explore

More to Explore