Westport holiday rentals

We found 1,920 holiday rentals — enter your dates for availability
Discover a selection of 23 homes and other holiday rentals in Westport that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as air conditioning and a pool. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Westport

Showing deals for:18 Dec - 25 Dec

Paquachuck Inn
back of the house, from the our dock
Bar (on property)
our dock
Exceptional
(6 reviews)

Relax by the sea! Bed & Breakfast near Horseneck State Beach

Westport Point

8% off
AU$23,764
for 7 nights, 1 room
AU$3,395 per night
includes taxes & fees
Relax by the sea! Bed & Breakfast near Horseneck State Beach
Kitchen and Upstairs Bay View Bedroom entry
Open Casual Living Space
27 ft tall ceilings with amazing natural lighting from the Ocean facing windows!
Open Atrium
Exceptional
(66 reviews)

Water View Modern Villa 8 minutes to Newport, Sleeps 8,Near Beaches! WiFi

Jamestown

8% off
AU$7,548
for 7 nights, 1 villa
AU$1,078 per night
includes taxes & fees
Water View Modern Villa 8 minutes to Newport, Sleeps 8,Near Beaches! WiFi
Large Private Kitchen and Dinning Room
5 Stimpson St with South and West Ocean views
Living area
Large Private Kitchen and Dinning Room
Exceptional
(64 reviews)

Stunning Private Beach House Walking Distance To Easton's Beach

Middletown

8% off
AU$24,435
for 7 nights, 1 home
AU$3,491 per night
includes taxes & fees
Stunning Private Beach House Walking Distance To Easton's Beach
Large pantry with fold out shelves, sliders to deck with grill/pool.
Nearby Castle Hill Inn-drinks or exquisite meals with incredible view
NEW huge kitchen , seats up to 12. Bay window overlooks pool. Sliders to deck.
Newport harbor
Exceptional
(79 reviews)

Private POOL, Central air, walk to beach, new kitchen, king MBR

Middletown

20% off
AU$6,315
for 7 nights, 1 home
AU$902 per night
includes taxes & fees
Private POOL, Central air, walk to beach, new kitchen, king MBR
Second Upstairs Bedroom Foldable Crib
Aerial View
Baby gates at all of the stairs
Storage Shed
Exceptional
(31 reviews)

Quahog Cottage- Full Home with a private yard

Middletown

7% off
AU$6,101
for 7 nights, 1 cottage
AU$872 per night
includes taxes & fees
Quahog Cottage- Full Home with a private yard
Private kitchen
Beach
Property grounds
Dining
Exceptional
(13 reviews)

Walk to the Beach - Serene Coastal Country Cottage

Middletown

8% off
AU$10,513
for 7 nights, 1 cottage
AU$1,502 per night
includes taxes & fees
Walk to the Beach - Serene Coastal Country Cottage
Terrace/patio
Living area
Living area
Private kitchen
Exceptional
(58 reviews)

Renovated 2 Bed Private Home Newport-Middletown Sleeps 6

Middletown

8% off
AU$2,971
for 7 nights, 1 home
AU$424 per night
includes taxes & fees
Renovated 2 Bed Private Home Newport-Middletown Sleeps 6
Exterior
The Esplanade with right of way to the beach in front of my compound
Living area
Living area
Exceptional
(106 reviews)

Surfside! Fantastic Beach House, Near Restaurants, Cliff Walk, Close to Downtown

Middletown

8% off
AU$9,716
for 7 nights, 1 home
AU$1,388 per night
includes taxes & fees
Surfside! Fantastic Beach House, Near Restaurants, Cliff Walk, Close to Downtown
Living room
View from front porch
Driveway for 2-3 cars.
Living room with Smart TV
Exceptional
(25 reviews)

Renovated Cottage-- steps away from the water

Tiverton

8% off
AU$3,794
for 7 nights, 1 cottage
AU$542 per night
includes taxes & fees
Renovated Cottage-- steps away from the water
Living area
Outdoor dining
Interior
Dining
Exceptional
(23 reviews)

Half mile to beach, Family & Pet Friendly

Middletown

7% off
AU$7,378
for 7 nights, 1 home
AU$1,054 per night
includes taxes & fees
Half mile to beach, Family & Pet Friendly
Exterior detail
Outdoor dining
King bed
Private kitchen
Wonderful
(40 reviews)

Walk to the Beach! Large beach house

Middletown

7% off
AU$6,851
for 7 nights, 1 home
AU$979 per night
includes taxes & fees
Walk to the Beach! Large beach house
Exterior
Mackerel Cove
Living area
Living area
Exceptional
(31 reviews)

Jamestown for beach, golf and sailing. WINTER RENTAL 2026

Jamestown

12% off
AU$6,770
for 7 nights, 1 home
AU$967 per night
includes taxes & fees
Jamestown for beach, golf and sailing. WINTER RENTAL 2026
Interior
Exterior
Terrace/patio
Interior
Exceptional
(22 reviews)

Stunning 4 bedroom with access to private beach

South Dartmouth

10% off
AU$7,701
for 7 nights, 1 home
AU$1,100 per night
includes taxes & fees
Stunning 4 bedroom with access to private beach
Exterior
Dining
Private kitchen
Living area
Exceptional
(5 reviews)

Fabulous 5-bedroom house next to Greenvale winery in charming middletown area.

Portsmouth

8% off
AU$10,197
for 7 nights, 1 home
AU$1,457 per night
includes taxes & fees
Fabulous 5-bedroom house next to Greenvale winery in charming middletown area.
Kitchen
Master Bedroom
Pool at night
Family Room
Exceptional
(26 reviews)

Completely Remodeled, Private salt water pool and SPA, walk to 1st and 2nd beach

Middletown

12% off
AU$10,353
for 7 nights, 1 home
AU$1,479 per night
includes taxes & fees
Completely Remodeled, Private salt water pool and SPA, walk to 1st and 2nd beach
Light-filled living room with comfortable seating for the whole group
Thoughtfully landscaped grounds surrounding the home
Gather on the deck at sunset -- outdoor dining and lounging with meadow views
Fully equipped modern kitchen with induction range and generous prep space
Exceptional
(5 reviews)

Spacious Light-Filled Coastal Retreat, 4BR/Sleeps 9, Near Beaches

Tiverton

8% off
AU$7,458
for 7 nights, 1 home
AU$1,065 per night
includes taxes & fees
Spacious Light-Filled Coastal Retreat, 4BR/Sleeps 9, Near Beaches
Finished Basement
Newport Harbor
Dining Room
Main Living Room.
Exceptional
(102 reviews)

Easton Point, Short Walk To First And Second Beach - RI Reg - RE.0208807.STR

Middletown

7% off
AU$3,459
for 7 nights, 1 home
AU$494 per night
includes taxes & fees
Easton Point, Short Walk To First And Second Beach - RI Reg - RE.0208807.STR
Property grounds
Afternoons on the deck!
Interior
1 bedroom and full bath downstairs and 3 bedrooms upstairs with 2 full baths
Exceptional
(181 reviews)

Be on the Beach! Awesome Oceanfront Living Close to Downtown Dining Amazing View

Middletown

8% off
AU$8,834
for 7 nights, 1 home
AU$1,262 per night
includes taxes & fees
Be on the Beach! Awesome Oceanfront Living Close to Downtown Dining Amazing View
Views make doing dishes enjoyable!
View from loft.
Property grounds
Marina
Exceptional
(52 reviews)

Waterfront, Dog-Friendly Cottage on the Cove. In safe, quiet neighborhood.

Portsmouth

8% off
AU$3,568
for 7 nights, 1 cottage
AU$510 per night
includes taxes & fees
Waterfront, Dog-Friendly Cottage on the Cove. In safe, quiet neighborhood.
Living area
Property grounds
Interior
Dining
Exceptional
(42 reviews)

Cozy Waterfront Home In Portsmouth

Portsmouth

8% off
AU$4,997
for 7 nights, 1 cottage
AU$714 per night
includes taxes & fees
Cozy Waterfront Home In Portsmouth
Room
Exterior
Living area
Interior
Exceptional
(9 reviews)

Beautiful Historic Home

Little Compton

8% off
AU$6,357
for 7 nights, 1 home
AU$908 per night
includes taxes & fees
Beautiful Historic Home
Living area
Exterior
Private kitchen
Terrace/patio
Exceptional
(86 reviews)

Water Views from nearly Every Room! 3BR 3BA Luxury in Portsmouth RI

Portsmouth

8% off
AU$4,195
for 7 nights, 1 home
AU$599 per night
includes taxes & fees
Water Views from nearly Every Room! 3BR 3BA Luxury in Portsmouth RI
Living area
Dining
Interior
Dining
Exceptional
(60 reviews)

Spacious secluded home-Central AC-new large deck-huge yard

Middletown

8% off
AU$7,854
for 7 nights, 1 home
AU$1,122 per night
includes taxes & fees
Spacious secluded home-Central AC-new large deck-huge yard
Interior
Terrace/patio
Living area
Property grounds
Exceptional
(57 reviews)

Spectacular views at a charming waterfront cottage!!

Portsmouth

8% off
AU$4,376
for 7 nights, 1 home
AU$625 per night
includes taxes & fees
Spectacular views at a charming waterfront cottage!!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The friendly city of Westport awaits you

Enjoy the wineries and other features of Westport. Well known for its riverfront, shopping and kayaking, this welcoming city won't disappoint. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Westport

Are you looking for things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Westport a one-of-a-kind holiday spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Westport Rivers Vineyard & Winery (0.7 mi / 1.1 km)
  • Coastal Vineyards (4.8 mi / 7.8 km)
  • Carolyn's Saskonnet Vineyard (6.6 mi / 10.6 km)
  • Coastal Roasters (8.2 mi / 13.2 km)
  • Newport International Polo (9.1 mi / 14.7 km)
  • Newport Vineyards (10.7 mi / 17.2 km)

Exploring the natural landscape of Westport

Whether you're looking for adventure or just want to appreciate the scenery, Westport is a great place to get out in nature. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Horseneck State Beach (4.5 mi / 7.2 km)
  • Gooseberry Island (6 mi / 9.7 km)
  • Goosewing Beach Preserve (6.1 mi / 9.8 km)
  • Rotch Jones-Duff House and Garden Museum (8.6 mi / 13.8 km)
  • Tappens Beach (9.2 mi / 14.9 km)
  • Lloyd's Beach (9.9 mi / 16 km)

Travelling to and around Westport

The nearest airport is in New Bedford, MA (EWB-New Bedford Regional), located 9.3 mi (15 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Newport, RI (NPT-Newport State), which is 11.2 mi (18 km) away.

Frequently asked questions

What is the best area to stay in Westport when booking a holiday rental?
When considering a holiday rental in Westport, Massachusetts, a popular area to stay is along the coastline near Westport Point. This picturesque neighbourhood offers stunning views of the Atlantic Ocean and the historic Westport River. Visitors can enjoy the charming atmosphere while being close to top attractions such as the beautiful Horseneck Beach State Reservation, great for sunbathing, swimming, and beachcombing. Additionally, the nearby Westport Rivers Vineyard & Winery provides a delightful experience for wine enthusiasts, offering tastings and tours amidst scenic landscapes.Another appealing area is the village centre, where you can immerse yourself in the local culture and community. This area features quaint shops, delightful eateries, and easy access to the Westport Town Farm, which is a great spot for those interested in local agriculture and sustainability.
Where are the best areas for renting a beach house in Westport?
For renting a beach house in Westport, Massachusetts, the area around Westport Point is particularly appealing. This charming coastal neighbourhood offers picturesque views of the Westport River and easy access to sandy beaches. Many properties here come equipped with amenities such as spacious decks for enjoying the sunset, outdoor grills for barbecues, and fully stocked kitchens, making them great for family gatherings or a relaxing retreat with friends.Another excellent option is the Horseneck Beach area, where visitors can find a variety of beach houses just a short walk from the shore. These rentals often include features like private pathways to the beach, outdoor showers, and ample parking. The nearby Horseneck Beach State Reservation provides opportunities for walking, picnicking, and enjoying the natural beauty of the coastline, enhancing the overall experience for beachgoers.In addition to beach access, Westport offers a laid-back atmosphere with local shops and eateries, allowing travellers to immerse themselves in the community.
What is the most popular type of holiday rental accomodation in Westport?
In Westport, holiday houses are the most popular type of holiday rental, with around 64 available throughout the area. These houses are often situated in serene neighbourhoods, providing a peaceful environment ideal for families and groups. Most properties come equipped with spacious layouts, full kitchens, and outdoor areas for enjoying the coastal breeze. Additionally, there are about 24 cottages available, which offer a charming and rustic experience, often featuring cosy interiors and close proximity to nature. There are also several apartments and condos, which cater to those looking for more compact accommodations.
Are there any family house rentals in Westport?
In Westport, Massachusetts, there are numerous family-friendly house rentals available, with around 11 options to choose from. This picturesque coastal town offers a charming environment, making it an ideal destination for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to play and explore.Visitors can enjoy amenities such as Wi-Fi, air conditioning, and often laundry facilities, ensuring a comfortable and convenient stay. The locale is close to beautiful beaches, where families can enjoy swimming and sunbathing, as well as parks that provide recreational opportunities.
Are there pet-friendly house rentals in Westport?
In Westport, there are several pet-friendly house rentals available, making it a great destination for travellers looking to enjoy a peaceful getaway with their furry companions. Many of these holiday rentals feature amenities that cater to both pets and their owners, such as spacious yards, outdoor seating areas, and sometimes even proximity to local pet-friendly beaches.The scenic coastal area offers stunning views and access to various outdoor activities, including walking trails along the shoreline, which are great for leisurely strolls with pets. Additionally, the local community is welcoming to dogs, with parks and open spaces where your pet can roam freely.For those seeking a more tranquil experience, the rentals often come equipped with modern conveniences like fully equipped kitchens, comfortable living spaces, and sometimes even outdoor grills for al fresco dining.
Are there any remote work holiday rentals in Westport?
In Westport, Massachusetts, there are a substantial number of remote work holiday rentals available—around 92 to choose from. This picturesque coastal town offers a tranquil environment, ideal for those looking to blend work and leisure. Many properties come equipped with high-speed internet, Wi-Fi, and dedicated workspaces, making it easy to stay productive during your stay.Visitors can enjoy the scenic beauty of the nearby beaches and the charming local atmosphere, with amenities often including comfortable living areas, fully equipped kitchens, and outdoor spaces for relaxation. The proximity to local attractions, such as the Westport Town Farm and the serene coastal landscapes, provides opportunities for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Westport?
In Westport, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy home-cooked dining experiences. Many properties also feature outdoor decks or patios, providing a lovely space to relax and take in the surrounding beauty. Onsite parking is typically available, which is convenient for those travelling by car. Additionally, rentals often include coffee and tea makers, ensuring that guests can start their day with a warm beverage.
When is the best time to visit Westport for a holiday rental?
The best time to visit Westport for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts families and beachgoers who flock to the picturesque shores of Westport to enjoy the sun, sand, and various outdoor activities. With warm temperatures often reaching the mid to high 20s Celsius, it's an ideal time for swimming, kayaking, and soaking up the coastal charm.In July, you can expect a lively option, with plenty of opportunities to engage in local events, explore the scenic coastline, or simply relax on the beach. The abundance of holiday rentals during this time ensures you'll find a comfortable spot to unwind after a day of adventure, whether you're enjoying a family barbecue or taking in the stunning sunsets over the Atlantic.If you're seeking a more tranquil experience, consider visiting in November. This month offers a quieter atmosphere, great for enjoying walks along the beach and exploring the beautiful natural surroundings without the summer crowds. Plus, you might find more competitive rental rates, providing great value for your getaway.
What are the top attractions in Westport?
In Westport, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's natural beauty and rich history. The Westport River offers opportunities for kayaking and fishing, with scenic views along its banks. The nearby Horseneck Beach State Reservation is a popular spot, featuring miles of sandy shoreline and excellent conditions for swimming, sunbathing, and birdwatching.The town is also home to several charming farms, such as the Westport Farmers' Market, where local produce and artisanal goods can be found. For those interested in history, the Westport Historical Society offers insights into the town's past with various exhibits and events.Additionally, the scenic coastal drive along Route 88 provides stunning views of the Atlantic Ocean, making it a great route for leisurely drives or bike rides.
Are all fees included in the Westport holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Westport holiday homes with parking?
Stayz offers a wide selection of holiday homes in Westport with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Westport holiday homes?
You can find great discounts on holiday homes in Westport on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Westport holiday home booking on Stayz?
To find Westport holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Westport?
A long-stay holiday home in Westport is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Westport holiday home?
Book your Westport holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Westport?
Prices for holiday homes in Westport vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Westport to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas