Holiday rentals in Watch Hill, Westerly

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Top-rated holiday rentals in Watch Hill, Westerly

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Guest favourite

Guest house 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.

4–11 Oct

$294 SGD per night

Guest favourite

Flat in Stonington

4.99 out of 5 average rating, 137 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.

1–8 Dec

$154 SGD per night

Guest favourite

Flat in Stonington

4.95 out of 5 average rating, 220 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!

4–11 Oct

$434 SGD per night

Guest favourite

Guest house 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.

8–15 Sep

$158 SGD per night

Guest favourite

Home in Stonington

4.95 out of 5 average rating, 166 reviews

Romantic Seaside Cottage in Mystic

This cozy seaside cottage with sleep loft has the look and feel of an old classic yacht inside with modern amenities. Couples will love the water views, screened porch, gas-wood stove, heated stone floor in cedar bathroom, outdoor shower and patio. Another larger 2 bedroom cottage on property is for rent also for families with younger children. This rental is NOT suitable for toddlers or children under 12 due to the open balconies, railings and narrow spiral staircase to the loft.

10–17 Jul

$440 SGD 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

28 Sep – 5 Oct

$196 SGD per night

Guest favourite

Guest suite in Stonington

4.99 out of 5 average rating, 140 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!

11–18 Oct

$322 SGD per night

Guest favourite

Flat in New London

4.98 out of 5 average rating, 289 reviews

Quiet Neighborhood home close to everything

Spacious & charming 2 bed RM APT on the 3rd fl of my home, gives you all the comforts of home while you’re away. We are a quick walk to L&M (Yale) Hospital, Mitchell College, And EB NL Campus. Short drive to the Coast Guard Academy, Conn College, Domion (Millstone) and The US Submarine Base. And if you’re here for fun, we are 1.5 miles to Ocean Beach (borrow our pass for free access) 20 min to Mohegan Sun & 25 to Foxwoods and 15 min to Mystic. Follow us on Insta at 199Thames.

21–28 Oct

$176 SGD per night

Guest favourite

Home in Westerly

4.97 out of 5 average rating, 101 reviews

South County House

South County House is a 1500 sq ft two bedroom, 1.5 bath cape built in 1936 that sits on nearly an acre of land, 3/4 of a mile from the ocean in Westerly, RI. It borders preserved forest, and there is a small family farm across the street. The house has been thoughtfully redesigned and renovated with relaxation in mind, and provides an ideal escape from the distractions and noise of modern life. Recently featured in Vogue, Architectural Digest, Travel + Leisure, Remodelista, etc.

4–11 Mar

$492 SGD per night

Guest favourite

Guest suite in Westerly

4.93 out of 5 average rating, 117 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.

1–8 Jan

$161 SGD per night

Guest favourite

Guest suite in New Shoreham

4.99 out of 5 average rating, 152 reviews

Hilltop Happiness

We are located high on Mott hill in the center of the island. It's about 2 miles to both harbors. There are lots of hiking trails nearby. We are located near the island airport so small private planes come and go during the day but it is usually very quiet at night. Many of our guests say watching the planes is one of their favorite things. This spot is ideal for visitors who like to retreat to a quieter space at the end of a long day at the beach or an evening on the town.

7–14 Oct

$228 SGD 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!

17–24 Dec

$217 SGD per night