Vacation rentals in Watch Hill, Westerly

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Top-rated vacation rentals in Watch Hill, Westerly

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Guesthouse in Stonington

4.97 out of 5 average rating, 222 reviews

True Artist Loft, 5 minutes to downtown Mystic

The Dacha, as it has lovingly been called for almost 80 years was built in 1945 originally as a studio for the artist that resided on the property. The unique structure is truly one of a kind, fully insulated for winter and tucked away from the road, sitting on a quiet piece of land, just 5 minutes to downtown Mystic. Enjoy modern comforts and a designers decor, while settling in front of the fire, or taking a short drive to all that Mystic has to offer- hiking, water, shops and restaurants.

Oct. 6 – 13

$330 CAD per night

Guest favourite

Apartment in Stonington

4.99 out of 5 average rating, 136 reviews

The Moss Farm-private apt- Pawcatuck/Stonington

This very private one bedroom apartment is on the second floor of a farmhouse built in 1714. Located in the village of Pawcatuck in Stonington, CT, it is walking distance to downtown Westerly, RI. A short drive to Mystic, Watch Hill, CT/RI beaches, & casinos. Connecticut College, US Coast Guard Academy and the Groton Sub Base are nearby. The apartment is comfortably furnished with a full size bed and pull out sofa to accommodate a party of four. Exposed beams add character to a modern space.

Oct. 3 – 10

$188 CAD per night

Guest favourite

Apartment in Stonington

4.95 out of 5 average rating, 218 reviews

Mystical Ocean View in Historic Stonington Borough

Enjoy stunning ocean views of Stonington Harbor and Fishers Island Sound from multiple floors of this spacious, comfortable apartment for 6. Located in historic Stonington Borough, Connecticut's oldest village, you can relax in the private library, then explore this picturesque area with acclaimed restaurants, shops, and museums all within walking distance. And with Downtown Mystic, I-95, and RI's beaches just a short drive away, you can have it all, located half way between Boston and NYC!

Nov. 25 – Dec. 2

$712 CAD per night

Guest favourite

Farm stay in North Stonington

4.99 out of 5 average rating, 134 reviews

Mystic Country Farm Stay

Escape to the tranquility of 100 Acre Wood, our charming historic farm retreat in Mystic Country, Connecticut. Owl's House is a private and stylish guest cottage nestled among the trees. Our farm store, stocked with local products, invites you to unwind and enjoy the bounty of the land. Enjoy picturesque views of the pastoral landscape and private forest trails, or get out and play in the area's abundance of fine dining, wineries, seasonal attractions, outdoor activities, and entertainment.

Dec. 19 – 26

$565 CAD per night

Guest favourite

Guesthouse in Charlestown

4.88 out of 5 average rating, 268 reviews

Cozy All Season Cabin Near Beach at Rockbriar Farm

Small vintage vacation cabin located in Charlestown, RI a 1 mile walk/bike to the town beach. Located on 7 acres called Rockbriar Farm, the cabin is in a wooded setting away from our home affording privacy for guests. One large room includes the futon bed/couch and the one sink; the shower and toilet are in separate room. Cabin also has a cedar enclosed hot water outdoor shower. Clean, cozy but not luxurious! No stove, but coffee maker, microwave, outside grill, and mini fridge.

Dec. 20 – 27

$156 CAD per night

Guest favourite

Guest suite in Stonington

4.98 out of 5 average rating, 108 reviews

The Beacon- Guest Suite

The Beacon is a nautically decorated private suite with over 700 square feet to relax in. Brand new (Built in 2022) clean studio that comes with all new amenities. It's a private space/private entrance attached to our home. The kitchen features a microwave, coffee maker, fridge and dishwasher. The space is equipped with WIFI and a SMART TV. 1.5 Miles to Westerly, RI 5.1 Miles to Misquamicut Beach 5.8 Miles to Mystic, CT 8.1 Miles to Foxwoods Casino 14 Miles to Mohegan Sun Casino

Feb. 11 – 18

$238 CAD per night

Guest favourite

Guest suite in Stonington

4.99 out of 5 average rating, 139 reviews

Morgan Suite

The Morgan Suite is a totally private Airbnb located in a quiet neighborhood along the Pawcatuck River. Minutes to downtown Westerly, downtown Mystic, beaches, breweries, wineries and much more. This Airbnb a perfect for a romantic getaway or a relaxing memorable vacation with friends. If you are looking to explore a new area and feel right at home, Morgan Suite is for you! The home is spacious, newly renovated with amenities that make you feel right at home. Newly added - hot tub!

Oct. 4 – 11

$393 CAD per night

Guest favourite

Guest suite in Westerly

4.93 out of 5 average rating, 115 reviews

Adorable in-law apartment with private entrance!

An adorable in-law apartment with a private entrance that's close to everything the beautiful town of Westerly has to offer. Come spend the night (or a few) in the very spacious studio equipped with a kitchen, full bathroom, and bedroom with a very comfortable queen bed. -Located 1 mile from historic downtown Westerly and only 4 miles from the beach. -Take a nice 10 minute drive to Mystic, CT. -Foxwoods Casino is 12 miles away. -Private entrance and parking on premises.

Jul. 6 – 13

$255 CAD per night

Guest favourite

Farm stay in Hopkinton

4.98 out of 5 average rating, 192 reviews

Farm with a few goats on a lake close to beaches.

This is a bright walk out apartment in our home with a private entrance. We will be here but we give you all the privacy that you want. I have recently lost 3 goats. I still have two goats. This is a rural town 7 miles from Westerly, Rhode Island, and about 12 miles from Mystic. Please read the whole description of this property to make sure it is suitable for your family. Please read my reviews. I think my guests describe the accommodation even better than I do!

Aug. 20 – 27

$244 CAD per night

Guest favourite

Apartment in Stonington

4.95 out of 5 average rating, 131 reviews

Waterfront Marina Living

Waterfront marina living in Stonington's oldest house. This 1650's post and beam home on Wequetequock Cove was originally a trading post. Use our kayaks to explore the cove and sheltered bay. Paddle to Saltwater Farm Vineyard up the Cove, or explore Barn Island Nature Preserve. Sandy Point, Napatree Beach, East Beach and Dubois Beach are close by car or boat. You're just minutes from Stonington Borough, Mystic, the Seaport, Mystic Aquarium, Westerly and Watch Hill.

Sep. 8 – 15

$307 CAD per night

Guest favourite

Guest suite in Westerly

4.98 out of 5 average rating, 62 reviews

Private suite close to beaches and downtown.

The Ruedemann Suite is situated off of our main house in a quiet neighborhood. We are located 3 miles from Misquamicut Beach & Watch Hill. Historic Downtown Westerly with its thriving restaurant, arts & music scene is 1.5 miles from the house. Take a short drive to Stonington or Mystic for shopping or local vineyards. Feeling lucky? Mohegan Sun & Foxwoods Casinos are close by! Newport & Providence are a 45-minute drive. Follow on the gram @ruedemannsuite

Dec. 12 – 19

$207 CAD per night

Guest favourite

Guest suite in Westerly

4.96 out of 5 average rating, 120 reviews

Room with a View on Spring Pond

Fab newly decorated suite in 1957 home set on a private pond near Watch Hill, RI. Private entrance with mini kitchen, fridge,microwave, portable induction cooktop,toaster,coffeemaker- every thing but the kitchen sink! Please note: there is no kitchen sink nor oven. Ensuite bath with new towels,robes,linens,and bedding. Outdoor shower ( in addition to an indoor one!) ,grill,lounging area. Near beaches,music,food, Mystic Ct attractions. Great relaxing venue.

Dec. 23 – 30

$442 CAD per night