Westerly holiday rentals

We found 783 holiday rentals — enter your dates for availability
Select from 106 homes, 31 cottages and other holiday rentals in Westerly to find one that's perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the amenities that you need and want, which might include parking and a hot tub. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Westerly

Showing deals for:22 Jan - 29 Jan

Room
Outdoor deck #2 next to master suite
Interior
Dining
Exceptional
(64 reviews)

Elevate your New England beach retreat experience - Mystic / Foxwoods / Mohegan

Groton

8% off
S$7,640
for 7 nights, 1 home
S$1,091 per night
includes taxes & fees
Elevate your New England beach retreat experience - Mystic / Foxwoods / Mohegan
Exterior
Kitchen and Dining Area
Kitchen and Dining Area
Backyard
Exceptional
(17 reviews)

Beach house, inground pool, hot tub, Large backyard,1.5 Miles from Misquamicut

Westerly

7% off
S$7,977
for 7 nights, 1 home
S$1,140 per night
includes taxes & fees
Beach house, inground pool, hot tub, Large backyard,1.5 Miles from Misquamicut
Private kitchen
Interior
Property grounds
Property grounds
Exceptional
(61 reviews)

Private Home in scenic Matunuck, RI within walking distance to Town Beach

South Kingstown

8% off
S$4,101
for 7 nights, 1 home
S$586 per night
includes taxes & fees
Private Home in scenic Matunuck, RI within walking distance to Town Beach
Exterior
Outdoor dining
Living area
Interior
Exceptional
(14 reviews)

Secluded Farmhouse Retreat - Minutes from Mystic

Stonington

7% off
S$4,846
for 7 nights, 1 home
S$692 per night
includes taxes & fees
Secluded Farmhouse Retreat - Minutes from Mystic
Central living room with flat screen, cable and Bose surround sound
Private kitchen
Dining area / kitchen
Screen porch overlooking pool
Exceptional
(26 reviews)

Beautiful Watch Hill 4BR/3BA with Backyard Deck & Pool Just Steps From Beach

Westerly

8% off
S$9,565
for 7 nights, 1 home
S$1,366 per night
includes taxes & fees
Beautiful Watch Hill 4BR/3BA with Backyard Deck & Pool Just Steps From Beach
Exterior
Dining
Interior
Living area
Exceptional
(6 reviews)

NEW! Historic Mystic, Two Minute Walk to Mystic Pizza!

Mystic

8% off
S$9,219
for 7 nights, 1 home
S$1,317 per night
includes taxes & fees
NEW! Historic Mystic, Two Minute Walk to Mystic Pizza!
Stunning Views All Around with High End Landscape Lighting For That Resort Feel!
Property grounds
A Cozy Coastal Great Room That All Family & Friends Can Enjoy.
True Cottage Charm With All The Comforts and Expansiveness
Exceptional
(57 reviews)

Luxury Waterfront Retreat, Private Dock, Beach Access & Stunning Views

South Kingstown

16% off
S$18,528
for 7 nights, 1 home
S$2,647 per night
includes taxes & fees
Luxury Waterfront Retreat, Private Dock, Beach Access & Stunning Views
Exterior
Living area
Living area
Interior
Exceptional
(97 reviews)

Casa De Las Olas - Cute cozy cottage in Westerly, RI

Westerly

7% off
S$2,233
for 7 nights, 1 cottage
S$319 per night
includes taxes & fees
Casa De Las Olas - Cute cozy cottage in Westerly, RI
Main floor living room
Build in 1729
Back yard patio
King bed in master
Exceptional
(24 reviews)

Historic John Burrows House in Downtown Mystic

Mystic

8% off
S$8,429
for 7 nights, 1 home
S$1,204 per night
includes taxes & fees
Historic John Burrows House in Downtown Mystic
Interior
Outdoor dining
Private kitchen
Exterior
Exceptional
(22 reviews)

Château Stonington

Stonington

7% off
S$7,379
for 7 nights, 1 home
S$1,054 per night
includes taxes & fees
Château Stonington
Outdoor dining
Private kitchen
Interior
Room
Exceptional
(29 reviews)

Welcome to Coastal Charm in beautiful Westerly, Rhode Island!

Westerly

16% off
S$3,298
for 7 nights, 1 home
S$471 per night
includes taxes & fees
Welcome to Coastal Charm in beautiful Westerly, Rhode Island!
Private kitchen
Living area
Room
Interior
Exceptional
(5 reviews)

Charming 3-bedroom townhome-like guest unit with AC and WiFi in QEBA

Charlestown

8% off
S$4,174
for 7 nights, 1 home
S$596 per night
includes taxes & fees
Charming 3-bedroom townhome-like guest unit with AC and WiFi in QEBA
Front porch
Front of the house
Sitting area
Exterior
Exceptional
(29 reviews)

Charming Colonial in the Heart of Mystic: Walk to Downtown, Sleeps 8

Mystic

7% off
S$5,981
for 7 nights, 1 home
S$854 per night
includes taxes & fees
Charming Colonial in the Heart of Mystic: Walk to Downtown, Sleeps 8
Exterior
Living area
Private kitchen
Terrace/patio
Exceptional
(29 reviews)

Mystic Pearl, Charming 4 Bedroom Home, Downtown Mystic

Mystic

8% off
S$3,680
for 7 nights, 1 home
S$526 per night
includes taxes & fees
Mystic Pearl, Charming 4 Bedroom Home, Downtown Mystic
Patio dining area
Living area
Private kitchen
Property grounds
Exceptional
(5 reviews)

Charming 3 bedroom house in Stonington

Pawcatuck

12% off
S$4,600
for 7 nights, 1 home
S$657 per night
includes taxes & fees
Charming 3 bedroom house in Stonington
Master bedroom--third floor. King bed
deck on a sunny morning
Third floor mezzanine, between bedroom and bathroom. Overlooks living area
living room is very sunny with two sets of sliding glass doors opening to deck
Exceptional
(82 reviews)

Sunny Scandinavian House on Wamphassuc Pt. Harbor view. Short walk to the beach

Stonington

8% off
S$3,980
for 7 nights, 1 home
S$569 per night
includes taxes & fees
Sunny Scandinavian House on Wamphassuc Pt. Harbor view. Short walk to the beach
Historic charm reimagined with modern coastal luxury
Beautiful sunrise mornings with the calming ocean breeze - steps from the beach
“Stroll from the School House to soft sand and rolling surf in seconds.”
“Unwind with cocktails and ocean breezes next door to the Ocean House Hotel.”
Exceptional
(6 reviews)

Watch Hill Luxury by the Sea, Iconic 1852 School House, Beside Ocean House Hotel

Westerly

8% off
S$14,688
for 7 nights, 1 home
S$2,098 per night
includes taxes & fees
Watch Hill Luxury by the Sea, Iconic 1852 School House, Beside Ocean House Hotel
Bedroom
Living/Dining Room + Deck
Kitchenette
Exterior
Exceptional
(15 reviews)

Contemporary Cottage

Westerly

7% off
S$2,802
for 7 nights, 1 cottage
S$400 per night
includes taxes & fees
Contemporary Cottage
Back yard
Front walkway with a lot of tree cover street-side, charming, quiet, corner lot
Freshly updated: new kitchen, new sofas, refinished floors, seats 12 comfortably
First look inside - airy, inviting space perfect for relaxing and gathering
Exceptional
(35 reviews)

3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa

Westerly

14% off
S$2,698
for 7 nights, 1 home
S$385 per night
includes taxes & fees
3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa
Property grounds
Property grounds
Interior
Private kitchen
Exceptional
(6 reviews)

Welcome to the Wood River Retreat! Newly remodeled apartment is a quiet area.

Hope Valley

7% off
S$2,109
for 7 nights, 1 apartment
S$301 per night
includes taxes & fees
Welcome to the Wood River Retreat! Newly remodeled apartment is a quiet area.
Exterior
Interior
Private kitchen
Living area
Exceptional
(65 reviews)

Beautiful Studio overlooking the Mystic River

Mystic

8% off
S$2,047
for 7 nights, 1 apartment
S$292 per night
includes taxes & fees
Beautiful Studio overlooking the Mystic River
Living area
Outdoor dining
Interior
Exterior
Exceptional
(7 reviews)

Mystic - Island retreat

Mystic

8% off
S$4,812
for 7 nights, 1 home
S$687 per night
includes taxes & fees
Mystic - Island retreat
Interior
Large french doors to covered patio
Living area
Enclosed sunroom
Exceptional
(21 reviews)

Coastal Hideaway in Charlestown - Beach house w/ Fire pit, 1 Mi from Beach

Charlestown

5% off
S$3,655
for 7 nights, 1 home
S$522 per night
includes taxes & fees
Coastal Hideaway in Charlestown - Beach house w/ Fire pit, 1 Mi from Beach
Outdoor dining
The property is right next to Schooner Wharf
Full kitchen with stainless appliances, coffee maker, hot water kettle
Std height dining table + high top
Exceptional
(59 reviews)

Exceptional location footsteps to beautiful downtown Mystic w/private driveway

Mystic

5% off
S$3,317
for 7 nights, 1 home
S$474 per night
includes taxes & fees
Exceptional location footsteps to beautiful downtown Mystic w/private driveway

  • 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 beachside setting of Westerly is ready to explore

Enjoy the live music and other features of Westerly. This city's beaches, sporting events and seaside draw many visitors. Foxwoods Resort Casino and Mohegan Sun Casino are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Westerly

Are you hoping to discover attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Westerly a fun spot to go on holiday. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Stonington Vineyard (4.3 mi / 6.9 km)
  • Mystic Aquarium and Institute for Exploration (6.6 mi / 10.6 km)
  • Lake of Isles (9.5 mi / 15.3 km)
  • Saltwater Farm Vineyard (3.8 mi / 6.1 km)
  • Ninigret (4.9 mi / 7.8 km)
  • Jonathan Edwards Winery (6.4 mi / 10.4 km)

Exploring the beaches and other natural features in Westerly

Whether you're an active traveller or just want to spend some time taking in the scenery, Westerly is a great place to get outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Misquamicut State Beach (4 mi / 6.4 km)
  • Atlantic Beach Park (4 mi / 6.4 km)
  • East Beach (4.7 mi / 7.6 km)
  • East Beach Watch Hill (5 mi / 8 km)
  • Weekapaug Beach (5.3 mi / 8.6 km)
  • Napatree Point (5.8 mi / 9.3 km)

Seasonal weather in Westerly

If warm-weather activities are high on your list, July, August, September and June are the hottest months to visit, when temperatures average 21°C.

How to get to and around Westerly

The nearest airport is in Westerly, RI (WST-Westerly State), located 2.2 mi (3.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into New London, CT (GON-Groton - New London), which is 11.8 mi (19 km) away.

If you'd prefer to travel by train, you can make your way to Westerly Station.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Westerly?
The most sought-after types of holiday rentals in Westerly are houses. Hoping for something different? Vrbo has plenty of options to match the diverse needs of our guests, so you'll see holiday properties in all shapes and sizes. The perfect fit is ready and waiting for you — lock in yours today.
How much does it cost to rent a holiday rental in Westerly?
The average price for a holiday rental in Westerly is based on a number of factors, such as property type, length of stay and time of year. Whether you prefer a villa with space for extended family or a cosy cottage for just you and your sweetheart, just enter your dates of travel to see stays with amazing value.
How much does it cost to rent a beach house in Westerly?
When you travel and the style and size of the property will determine the cost of your beachside stay. Enter your Westerly travel dates to see your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use the filters to select the amenities and features you want in your rental.
Are there pet-friendly holiday rentals in Westerly?
Pack up a suitcase for your pup because Westerly has 106 properties that throw out the welcome mat to pets. Let your four-legged pal enjoy the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Westerly?
Add a whole other level of fun to your adventure by booking one of the 14 houses with a private pool in Westerly. Use our search filter to find the kind of property you want on Vrbo, and then spend lazy days splishing and splashing in a swimming pool that's just for you.
What are popular rental amenities in Westerly?
An electric car charging station, a barbecue grill and an ocean view rank as the most popular rental amenities in Westerly. Whether you plan to travel by yourself, with your spouse or a group of dear friends, Vrbo will help you find a holiday home that fits your style with all the features you're looking for.
Are there large group holiday rentals in Westerly?
Pick from 19 holiday homes in Westerly that can host 10 or more guests. Whether you're planning time away with extended family or a celebration like an anniversary, there's ample space to get your group together under the same roof.
Are there holiday rentals in Westerly that welcome kids?
With 106 family-friendly holiday homes to select from in Westerly, now is the perfect time to introduce the kiddos to the pleasures of travel. Click on our "Properties good for families" filter to locate stays packed with conveniences ideal for holidaying families, like living rooms, patios, bunk beds and entertainment areas.
What are the top attractions for families in Westerly?
Keeping the kids occupied during your Westerly holiday is child's play with these family-friendly attractions:
  • Mystic Seaport
  • Mystic Aquarium and Institute for Exploration
  • Misquamicut State Beach
Are there one-bedroom holiday rentals in Westerly?
Westerly has 11 one-bedroom rentals available. Usually situated in prime spots thanks to their smaller size, a one-bedroom holiday rental is great if you're getting away with your partner or a friend. And with comforts like laundry facilities and more privacy than a standard hotel, you'll be able to kick back and relax while exploring this terrific destination.
Can I find two-bedroom holiday rentals in Westerly?
Gather your loved ones and enjoy total privacy and comfort in one of the 31 two-bedroom holiday rentals Westerly has to offer.
Are there holiday rentals with WiFi in Westerly?
Whether you want to keep up with the latest news, make a video call or update your social media, there are 39 holiday homes with WiFi in Westerly. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Westerly?
You can choose from 79 Vrbo holiday homes with air conditioning in Westerly providing that cool, cool breeze and extra element of comfort. Enter your desired travel dates and then use our handy filters to help you book stays with air conditioning.
How old do you have to be to rent a holiday rental in Westerly?
It's advisable to check with the Westerly holiday home you'd like on Vrbo as age restrictions differ. However, it's normally 16, 18 or 21.
How long can I rent a holiday rental in Westerly for?
How long you can book a holiday rental in Westerly varies according to the property. Just enter your desired dates to view a list of options offering extended stays. With many features like full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere perfect to call your home away from home in Westerly.

More holiday ideas