Two swans on a calm lake at sunset.

Westerly Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Westerly holiday rentals

A beach with waves gently lapping onto the shore under a clear sky.

1. Beach Cottage 1 Mile From Weekapaug & Misquamicut

Beach Cottage 1 Mile From Weekapaug & Misquamicut
Westerly
8.8 out of 10, Excellent, (197 reviews)
"This place met all our needs. "
United States
Andrea G.
The price is AU$618
includes taxes & fees
13 Sept - 14 Sept
Beach Cottage 1 Mile From Weekapaug & Misquamicut
A coastal town with a marina, sandy beach, and residential buildings.

2. Ocean Shire ☆ Beach Pass - Flex Check-in & out ꕀ Kids & Pet Welcome!

Ocean Shire ☆ Beach Pass - Flex Check-in & out ꕀ Kids & Pet Welcome!
Westerly
10.0 out of 10, Exceptional, (7 reviews)
"The place was so clean and neat. Barbara was very communicative and accommodating. Wonderful place in Westerly."
United States
Amy V.
Ocean Shire ☆ Beach Pass - Flex Check-in & out ꕀ Kids & Pet Welcome!
A room with a wooden bench, a small table, and a white perforated partition.

3. Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!

Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!
Westerly
9.2 out of 10, Wonderful, (18 reviews)
"Great spot, easy check-in and out, coffee, creamer, and sugar, snacks and water! Would recommend this for a 1/2 person stay! Great price!"
United States
Kelly A.
The price is AU$256
includes taxes & fees
8 Sept - 9 Sept
Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!
A two-story house with a dark siding exterior, white trim around windows and doors, and a small front yard with a lawn and a raised flower bed.

4. Brand new home close to Charlestown/Westerly beaches.

Brand new home close to Charlestown/Westerly beaches.
Westerly
9.8 out of 10, Exceptional, (47 reviews)
"House was clean, stocked with towels and clean sheets and plenty of essentials. Close to Westerly and Charlestown and not too far from Foxwoods. Great yard out back. Would love to stay again!"
United States
Will F.
The price is AU$1,321
includes taxes & fees
16 Sept - 17 Sept
Brand new home close to Charlestown/Westerly beaches.
An outdoor covered patio with wicker furniture and string lights.

5. Westerly Retreat

Westerly Retreat
Westerly
9.8 out of 10, Exceptional, (12 reviews)
"Great home, great host, no complaints."
United States
Gavin M.
The price is AU$1,563
includes taxes & fees
8 Sept - 9 Sept
Westerly Retreat
A two-story house with a porch and a wooden picnic table in the front yard.

6. Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Stonington
9.8 out of 10, Exceptional, (186 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is AU$402
includes taxes & fees
15 Sept - 16 Sept
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
A dock with a chair and a red canoe, overlooking a calm lake at sunset.

7. Lakeside cottage ON the water with beautiful views up the lake!

Lakeside cottage ON the water with beautiful views up the lake!
Ledyard
9.8 out of 10, Exceptional, (206 reviews)
"Sweet, cozy and clean. We had a nice time fishing, spotted a wide variety of birds, and enjoyed a few rounds of croquet. The lake was peaceful and quiet but is only a few minutes from the Foxwoods complex for shopping, dining, casino and shows. Thanks for a great stay!"
United States
Marcy P.
The price is AU$518
includes taxes & fees
10 Sept - 11 Sept
Lakeside cottage ON the water with beautiful views up the lake!
A spacious living room with a large sliding glass door leading to an outdoor patio.

8. Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage

Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage
West Mystic
10.0 out of 10, Exceptional, (24 reviews)
"Fantastic place to stay. "
United States
Cathy M.
The price is AU$445
includes taxes & fees
9 Sept - 10 Sept
Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage
A wooden porch with wicker furniture and a small table, overlooking a green lawn and a house in the background.

9. Perfect Group Escape · Coastal Mystic Ranch

Perfect Group Escape · Coastal Mystic Ranch
Mystic
10.0 out of 10, Exceptional, (39 reviews)
"It was a wonderful stay! Perfect location, amenities and fun!"
United States
Julie S.
The price is AU$889
includes taxes & fees
9 Sept - 10 Sept
Perfect Group Escape · Coastal Mystic Ranch
A deck with a grill, a glass table, and kayaks by a lake.

10. Lakeside cottage overhanging the water, beautiful window views across the lake

Lakeside cottage overhanging the water, beautiful window views across the lake
Ledyard
9.8 out of 10, Exceptional, (234 reviews)
"The kids had a blast fishing off the dock, very clean and comfortable"
United States
katlyn w.
The price is AU$501
includes taxes & fees
8 Sept - 9 Sept
Lakeside cottage overhanging the water, beautiful window views across the lake
A cozy living room with a fireplace, a large mural of a sailboat on water, and a view of the outdoors through a window.

11. 1784 Denison Home~ New England Nautical Inspiration~ Welcome to Warm Hospitality

1784 Denison Home~ New England Nautical Inspiration~ Welcome to Warm Hospitality
Stonington
10.0 out of 10, Exceptional, (75 reviews)
"I can't say enough about this amazing property and Debbie and Paul. The attention to detail both in the house and our every need was top notch. Thank you so much, we'll be back!"
United States
Julie T.
The price is AU$1,528
includes taxes & fees
9 Sept - 10 Sept
1784 Denison Home~ New England Nautical Inspiration~ Welcome to Warm Hospitality
A hammock in a lush garden with a house in the background.

12. A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!
Old Mystic
10.0 out of 10, Exceptional, (11 reviews)
"The place was perfect and the vibe was awesome. The hosts think of everything!"
United States
Matt F.
The price is AU$333
includes taxes & fees
28 Sept - 29 Sept
A Mystic Stay as Sweet as Apple Pie!
A modern kitchen with white cabinetry, stainless steel appliances, and a wooden island.

13. Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.

Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Stonington
10.0 out of 10, Exceptional, (70 reviews)
"Great spot in walking distance to everything in Mystic!!"
United States
Mike O.
The price is AU$960
includes taxes & fees
21 Sept - 22 Sept
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
An aerial view of a coastal area with a beach, clear waters, and a small settlement with buildings and vehicles.

14. Charlestown Beach, 2BR Cozy Cottage, Screened porch, 3 min drive to Beach!

Charlestown Beach, 2BR Cozy Cottage, Screened porch, 3 min drive to Beach!
Charlestown
10.0 out of 10, Exceptional, (29 reviews)
"My family and I had an amazing time at the cottage. The host was very communicative and responsive. The cottage was clean, comfortable, and perfect for our stay in Charlestown."
United States
Erinn
The price is AU$785
includes taxes & fees
6 Oct - 7 Oct
Charlestown Beach, 2BR Cozy Cottage, Screened porch, 3 min drive to Beach!
A pathway leading to a building with an American flag, surrounded by lush greenery and potted plants.

15. Welcome to Williams Home & Smith Cottage- A Nautical New England Inspiration!

Welcome to Williams Home & Smith Cottage- A Nautical New England Inspiration!
Old Mystic
10.0 out of 10, Exceptional, (9 reviews)
"Clean prpoperty, close to all the fun places, very happy with our stay"
United States
salman z.
The price is AU$1,620
includes taxes & fees
29 Sept - 30 Sept
Welcome to Williams Home & Smith Cottage- A Nautical New England Inspiration!
A kitchen with a double sink, wooden countertops, a window with a view, and a clock on the wall.

16. Charming Historic House in Downtown Mystic

Charming Historic House in Downtown Mystic
Mystic
10.0 out of 10, Exceptional, (186 reviews)
"A wonderful stay "
United States
Gina P.
The price is AU$712
includes taxes & fees
23 Sept - 24 Sept
Charming Historic House in Downtown Mystic
A small kitchen with a view of the water, a bar area with stools, and a sign that reads "the BLUFFS".

17. Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY

Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY
West Mystic
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful place for family fun!"
United States
nancy m.
The price is AU$618
includes taxes & fees
8 Sept - 9 Sept
Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY
A marina with several sailboats docked, surrounded by houses and greenery.

18. LUX, Fireplace, Deck, Foosball, Pingpong, Private, Firepit, Multi-Gen Layout

LUX, Fireplace, Deck, Foosball, Pingpong, Private, Firepit, Multi-Gen Layout
West Mystic
10.0 out of 10, Exceptional, (37 reviews)
"Sparkling clean, well stocked, exactly as advertised property. The owner is responsive and easy to communicate with. Beautiful property! "
United States
Shirley M.
The price is AU$1,617
includes taxes & fees
8 Sept - 9 Sept
LUX, Fireplace, Deck, Foosball, Pingpong, Private, Firepit, Multi-Gen Layout
A two-story blue house with a central entrance, a small porch, and a garden with daffodils.

19. Historic Mystic Maritime House - 5 min Walk to Downtown Restaurants and Seaport

Historic Mystic Maritime House - 5 min Walk to Downtown Restaurants and Seaport
Mystic River Historic District
10.0 out of 10, Exceptional, (9 reviews)
"Great time and amazing space!"
United States
David G.
The price is AU$2,164
includes taxes & fees
9 Sept - 10 Sept
Historic Mystic Maritime House - 5 min Walk to Downtown Restaurants and Seaport
A modern living room with a sofa, coffee table, and a small side table with a lamp. There is a kitchen area with a dining table and bar stools.

20. Upscale Apartment in Mystic 7 Minute Walk to Drawbridge

Upscale Apartment in Mystic 7 Minute Walk to Drawbridge
Stonington
10.0 out of 10, Exceptional, (36 reviews)
"Great location, quite area, walking to everything downtown highly recommended."
United States
Chad L.
The price is AU$566
includes taxes & fees
9 Sept - 10 Sept
Upscale Apartment in Mystic 7 Minute Walk to Drawbridge
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.
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Top Westerly Hotel Reviews

Two Trees Inn

Two Trees Inn

8/10 Good
"Property was great. The rooms spacious. Breakfast was more like a family event than individual- loved that’s. Overall my family enjoyed the stay"
Elaine 3-night trip
Posted 3 hours ago
Two Trees Inn

Find out more about Westerly

Everything you need to know about Westerly holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Westerly holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Westerly holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Westerly holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westerly. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westerly holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westerly holiday rentals we have selected for you start as low as AU$387 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Westerly rentals

At Expedia, we put the best Westerly holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Westerly rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Westerly holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Westerly. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Westerly?

Yes, there are holiday rentals in Westerly close to The Flying Horse Carousel, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Westerly speak positively about the popular beaches and top-notch restaurants in this destination. While you're here, grab a bite or have a drink at the bars.

What are some of the best holiday rentals that Westerly has to offer?

Amazing Ocean Front 2 Story Home, Steps Away From The Water: This highly rated holiday home rental in Westerly is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind. Another good choice for your trip to Westerly is Beach Cottage 1 Mile From Weekapaug & Misquamicut.

How many holiday rentals are there in Westerly?

Choose from 106 Expedia holiday rentals in Westerly for a memorable holiday.

What can I see and do in Westerly?

Enjoy the outdoors at Misquamicut State Beach and Atlantic Beach Park, or simply take in cultural attractions like Babcock-Smith House and Granite Theatre. Other popular places to visit in the area include Foxwoods Resort Casino and Mohegan Sun Casino.

What are holiday rentals like in Westerly?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westerly. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family gatherings.