Two swans on a calm lake at sunset.

Westerly Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Westerly vacation homes

A two-story house with a front porch, a black door, and a mailbox.

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

3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa
Westerly
9.8 out of 10, Exceptional, (33 reviews)
"We will be back! great, responsive owners, phenomenal property and location! Go get breakfast at The Eatery down the road, it’s amazing!!"
United States
Travis C.
3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa
A two-story house with a porch and a wooden picnic table in the front yard.

2. 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, (190 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is CA $157
CA $383 total
includes taxes & fees
Sep 30 - Oct 1
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
A covered porch with wooden chairs and a bench, overlooking a street with cars and houses.

3. Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Mystic River Historic District
9.8 out of 10, Exceptional, (178 reviews)
"Great location "
United States
Brian S.
The price is CA $177
CA $403 total
includes taxes & fees
Sep 30 - Oct 1
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

4. The Blue Anchor House · walk Mystic-Train/Aquarium

The Blue Anchor House · walk Mystic-Train/Aquarium
Stonington
10.0 out of 10, Exceptional, (10 reviews)
"The house was clean, spacious and the location was perfect for all of our needs. Host was responsive when we reached out. Would definitely stay here again, and plan to in the future. "
United States
Bethany M.
The price is CA $273
CA $654 total
includes taxes & fees
Oct 5 - Oct 6
The Blue Anchor House · walk Mystic-Train/Aquarium
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.

5. 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 CA $636
CA $1,382 total
includes taxes & fees
Sep 30 - Oct 1
Brand new home close to Charlestown/Westerly beaches.
A kitchen with a double sink, wooden countertops, a window with a view, and a clock on the wall.

6. Charming Historic House in Downtown Mystic

Charming Historic House in Downtown Mystic
Mystic
10.0 out of 10, Exceptional, (191 reviews)
"A wonderful stay "
United States
Gina P.
The price is CA $368
CA $659 total
includes taxes & fees
Oct 19 - Oct 20
Charming Historic House in Downtown Mystic
A modern kitchen with white cabinetry, stainless steel appliances, and a wooden island.

7. 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, (73 reviews)
"Loved our stay, beautifully decorated inside and out. Conveniently located and so much within walking distance."
United States
Deborah J
The price is CA $509
CA $997 total
includes taxes & fees
Sep 30 - Oct 1
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
A cozy living room with a brown leather sofa, a potted plant, and a spiral staircase.

8. The Horse Carriage 2 miles from Foxwoods Casino

The Horse Carriage 2 miles from Foxwoods Casino
Preston
10.0 out of 10, Exceptional, (4 reviews)
"Super short stay but welcoming, clean and convenient for location"
United States
Christina S.
The price is CA $255
CA $603 total
includes taxes & fees
Sep 30 - Oct 1
The Horse Carriage 2 miles from Foxwoods Casino
A two-story house with a covered patio area, a front door, and a mailbox.

9. Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.4 out of 10, Exceptional, (69 reviews)
"It was great ocation for a weekend get away with friends to Mohegan Sun"
United States
Teresa M.
The price is CA $163
CA $391 total
includes taxes & fees
Sep 30 - Oct 1
Cozy, comfy,quiet &close to casinos
A waterfront restaurant with outdoor seating and a view of the water.

10. Charming 2 BR Green Hill Beach Cottage

Charming 2 BR Green Hill Beach Cottage
Green Hill
10.0 out of 10, Exceptional, (12 reviews)
"It was quiet and relaxing. Things looked as described and it was a good weekend getaway"
United States
Allicia H.
The price is CA $277
CA $609 total
includes taxes & fees
Oct 1 - Oct 2
Charming 2 BR Green Hill Beach Cottage
A modern living room with a large wooden dining table, a stone fireplace, a sofa, and a view of a lake through large windows.

11. Thames River Cottage · Near Casinos - USCGA

Thames River Cottage · Near Casinos - USCGA
Montville
10.0 out of 10, Exceptional, (3 reviews)
"A lovely quick overnight."
United States
Bonnie H.
The price is CA $193
CA $493 total
includes taxes & fees
Sep 30 - Oct 1
Thames River Cottage · Near Casinos - USCGA
A covered patio with a wooden table and white chairs, large windows, and a view of a deck and trees.

12. The Mystic Harbor House · walk downtown Mystic · train · aquarium

The Mystic Harbor House · walk downtown Mystic · train · aquarium
Stonington
9.8 out of 10, Exceptional, (11 reviews)
"Great house in a fantastic location. Very clean and well supplied. We would definitely stay here again."
United States
David C.
The price is CA $381
CA $782 total
includes taxes & fees
Oct 27 - Oct 28
The Mystic Harbor House · walk downtown Mystic · train · aquarium
A modern kitchen with white cabinets, a central island with stools, and a dining area with a table and chairs.

13. NEW! Updated Mystic Home w/ Sauna, Hot Tub & Deck

NEW! Updated Mystic Home w/ Sauna, Hot Tub & Deck
Groton
10.0 out of 10, Exceptional, (45 reviews)
"Very clean and well kept property. The hosts were very responsive. Would stay here again!"
United States
Holli
The price is CA $454
CA $1,099 total
includes taxes & fees
Oct 15 - Oct 16
NEW! Updated Mystic Home w/ Sauna, Hot Tub & Deck
A two-story beach house with a balcony, a wooden fence, and a sandy beach in the background.

14. Ocean Front Beach Cottage; Pets welcome

Ocean Front Beach Cottage; Pets welcome
Charlestown
9.6 out of 10, Exceptional, (34 reviews)
"We had a blast - great location, gorgeous beach!"
United States
Tara G.
The price is CA $396
CA $839 total
includes taxes & fees
Sep 30 - Oct 1
Ocean Front Beach Cottage; Pets welcome
A cozy room with a fireplace, red armchairs, a Christmas tree, and nautical decor.

15. Historic 1807 Williams Home... A Nautical New England Inspiration!

Historic 1807 Williams Home... A Nautical New England Inspiration!
Old Mystic
10.0 out of 10, Exceptional, (12 reviews)
"We had a great time at the house. We loved looking at all the great treasures and were impressed with how clean and well appointed the home is. Everyone loved our stay and Debbe was very responsive and helpful."
United States
Brett C.
The price is CA $484
CA $1,175 total
includes taxes & fees
Oct 14 - Oct 15
Historic 1807 Williams Home... A Nautical New England Inspiration!
A cozy cabin interior with a stone wall, wooden ceiling, and a fireplace. There is a staircase leading to an upper level.

16. Beautiful Cabin @ Fox Landing, near casinos

Beautiful Cabin @ Fox Landing, near casinos
Preston
9.8 out of 10, Exceptional, (19 reviews)
"Property was quiet and relaxing, overall great experience."
United States
Jeremy L.
The price is CA $255
CA $731 total
includes taxes & fees
Oct 6 - Oct 7
Beautiful Cabin @ Fox Landing, near casinos
A kitchen with a large island, wooden beams, white cabinetry, and a view to the outside.

17. Coastal Antique farmhouse

Coastal Antique farmhouse
North Stonington
9.2 out of 10, Wonderful, (7 reviews)
"simply beautiful, the yard, the kitchen, the bathroom in every bed-room. The house is just full of charm. We rented it for our family traveling from Boston to attend my son's wedding, and we couldn't have been happier! Would love to find a reason to return"
United States
beth g.
The price is CA $563
CA $1,550 total
includes taxes & fees
Oct 20 - Oct 21
Coastal Antique farmhouse
A living room with a fireplace, a grey armchair, and a large window.

18. Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (13 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is CA $239
CA $644 total
includes taxes & fees
Sep 30 - Oct 1
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
A white house with green shutters, a red door, and a flag.

19. Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!

Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!
Mystic River Historic District
10.0 out of 10, Exceptional, (97 reviews)
"Great location responsive hosts fully stocked cozy accommodations "
United States
dolly o.
The price is CA $515
CA $1,227 total
includes taxes & fees
Oct 5 - Oct 6
Historic 1810 Captain Burrows Home~ A Nautical New England Inspiration!
A small kitchen with a view of the water, a bar area with stools, and a sign that reads "the BLUFFS".

20. 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 CA $706
CA $909 total
includes taxes & fees
Oct 4 - Oct 5
Harbor View Landing Mystic, CT - The Bluffs Waterfront House - First Floor ONLY
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Westerly Hotel Reviews

Two Trees Inn

Two Trees Inn

10/10 Excellent
"Loved the pool area, convenience to casino, cleanliness, restaurant, and remodeled rooms. I thought the dog charge of 150 for one night was steep"
Karen 2-night trip
Posted 1 hour ago
Two Trees Inn

Find out more about Westerly

Westerly Vacation Homes information

Number of reviews
937
Accommodation
894 Vacation Homes
Lowest Price
CA $383
Highest Price
CA $1,550

Explore a world of travel with Expedia