Watch Hill, Westerly vacation rentals

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Top-rated vacation rentals in Watch Hill, Westerly

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

Guest favorite

Guesthouse in Stonington

4.98 out of 5 average rating, 217 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.

Sep 5 – 12

G$43,903 GYD per night
Guest favorite

Cottage in Waterford

4.99 out of 5 average rating, 104 reviews

Classic CT Cottage w/ Trail by Harkness Park/Ocean

Tastefully appointed! A quaint cottage in a forest setting on 6 acres bordering Harkness State Park. A peaceful & serene setting where you can hear nature by day and the lighthouse sound signal at night. The cottage is fully equipped & very comfortable for your stay. The Waterford beach is a short drive away...less than 2 miles through the forest...as are beautiful hikes along the coast. Centrally located near Historic Mystic, Niantic, Conn College, US Coast Guard Academy & the US Naval Base.

Apr 12 – 19

G$31,714 GYD per night
Guest favorite

Apartment in Stonington

4.99 out of 5 average rating, 134 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.

Mar 2 – 9

G$23,529 GYD per night

Popular amenities for Watch Hill, Westerly vacation rentals

Stay near Watch Hill, Westerly's top sights

Ocean House64 locals recommend
Watch Hill Lighthouse7 locals recommend
Olympia Tea Room26 locals recommend
Watch Hill Merry Go Round & Beach15 locals recommend
St Clair Annex Inc14 locals recommend
Ten Sandwiches3 locals recommend

Watch Hill, Westerly house rentals

Guest favorite

Home in Westerly

4.96 out of 5 average rating, 304 reviews

BarreCoast Stay: beach pass, casinos, vineyards

Apr 16 – 23

G$41,729 GYD per night
Guest favorite

Home in Preston

4.96 out of 5 average rating, 595 reviews

Entire House Magical Waterfront Getaway

Dec 29 – Jan 5

G$38,485 GYD per night
Guest favorite

Home in Stonington

4.97 out of 5 average rating, 181 reviews

Perfect New England Getaway has a pool/ hot tub

Dec 4 – 11

G$108,159 GYD per night
Guest favorite

Home in Stonington

4.94 out of 5 average rating, 123 reviews

Eco Friendly 1700s home! 0.3 miles to Westerly RI!

Mar 1 – 8

G$47,803 GYD per night
Guest favorite

Home in North Stonington

4.98 out of 5 average rating, 103 reviews

The Perch

May 6 – 13

G$80,299 GYD per night
Guest favorite

Home in Stonington

4.92 out of 5 average rating, 232 reviews

🧭 Newly Remodeled Home Near Westerly and Mystic

Jun 25 – Jul 2

G$56,345 GYD per night
Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 103 reviews

Walk to the beach at Black Point, Niantic, Ct

Mar 3 – 10

G$31,786 GYD per night
Guest favorite

Home in Montauk

4.87 out of 5 average rating, 176 reviews

Laid-Back Bungalow. 10 min Walk to Beach & Town!

Feb 12 – 19

G$108,159 GYD per night
Guest favorite

Home in Charlestown

4.95 out of 5 average rating, 118 reviews

Spacious RI Beach Escape

Jun 2 – 9

G$85,241 GYD per night
Guest favorite

Home in Lyme

4.97 out of 5 average rating, 185 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

Sep 28 – Oct 5

G$72,898 GYD per night
Superhost

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Blue Bay Dream - Apt #2

Jan 23 – 30

G$16,403 GYD per night
Guest favorite

Home in Stonington

4.99 out of 5 average rating, 168 reviews

Beautiful Modern Cape Downtown Mystic

Dec 12 – 19

G$63,380 GYD per night

Watch Hill, Westerly beach vacation rentals

Guest favorite

Guest suite in Westerly

4.96 out of 5 average rating, 120 reviews

Room with a View on Spring Pond

Nov 16 – 23

G$61,480 GYD per night
Guest favorite

Apartment in Stonington

4.95 out of 5 average rating, 131 reviews

Waterfront Marina Living

Aug 30 – Sep 6

G$38,281 GYD per night
Guest favorite

Cottage in South Kingstown

4.93 out of 5 average rating, 107 reviews

The Snug Cottage: Walk to Water-Newly Renovated

Sep 9 – 16

G$33,938 GYD per night
Guest favorite

Cottage in South Kingstown

4.92 out of 5 average rating, 133 reviews

THE WHITECAP COTTAGE

Oct 12 – 19

G$30,227 GYD per night
Guest favorite

Guest suite in Narragansett

4.89 out of 5 average rating, 399 reviews

Private Suite

Apr 2 – 9

G$21,983 GYD per night
Guest favorite

Guesthouse in Groton

4.94 out of 5 average rating, 381 reviews

Quiet studio with sleeping loft and deck

Jul 9 – 16

G$25,556 GYD per night
Guest favorite

Apartment in New London

4.98 out of 5 average rating, 288 reviews

Quiet Neighborhood home close to everything

Oct 23 – 30

G$27,630 GYD per night
Guest favorite

Apartment in New London

4.89 out of 5 average rating, 262 reviews

The Whaler’s Loft · Ocean Beach, Mystic & USCGA

Apr 15 – 22

G$32,625 GYD per night
Guest favorite

Vacation home in New London

5.0 out of 5 average rating, 108 reviews

Modern & Cozy Beach House - Walk to Ocean Beach

Sep 12 – 19

G$54,484 GYD per night
Guest favorite

Apartment in Newport

4.95 out of 5 average rating, 264 reviews

"ROOM AT BOB'S'

Dec 23 – 30

G$31,575 GYD per night
Guest favorite

Apartment in Middletown

4.98 out of 5 average rating, 266 reviews

Country Charm yet minutes to Newport

Nov 6 – 13

G$30,466 GYD per night
Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 582 reviews

Walk to Vineyards, Beaches, Farms & Town

Aug 27 – Sep 3

G$33,932 GYD per night

Beach house rentals in Watch Hill, Westerly

Guest favorite

Home in East Hampton

4.96 out of 5 average rating, 187 reviews

Ritz-East Hampton Cottage- 5 stars

Aug 28 – Sep 4

G$167,685 GYD per night
Guest favorite

Home in Mystic

4.94 out of 5 average rating, 168 reviews

Walk to Downtown Mystic - 3 bedrooms/2 full baths

Nov 3 – 10

G$71,560 GYD per night
Guest favorite

Home in Groton

4.95 out of 5 average rating, 156 reviews

True Ocean Front Vacationing - Groton/Mystic

Jan 23 – 30

G$95,973 GYD per night
Superhost

Home in Aquinnah

4.98 out of 5 average rating, 124 reviews

Martha's Vineyard Oceanview Retreat

Apr 14 – 21

G$120,825 GYD per night
Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 161 reviews

Beachfront Paradise

Nov 19 – 26

G$90,133 GYD per night
Guest favorite

Home in Greenport

4.98 out of 5 average rating, 162 reviews

Nofo Bungalow-In The Heart of Greenport Village

Sep 9 – 16

G$119,868 GYD per night
Guest favorite

Home in Westerly

5.0 out of 5 average rating, 18 reviews

Newly renovated cottage! 0.2 mi walk to the beach!

Sep 24 – Oct 1

G$76,224 GYD per night
Guest favorite

Home in Westerly

4.96 out of 5 average rating, 55 reviews

Modern Beach House in Westerly, RI

Nov 23 – 30

G$205,355 GYD per night
Guest favorite

Home in Stonington

4.9 out of 5 average rating, 79 reviews

Waterfront Home, Mystic, CT

Apr 27 – May 4

G$100,724 GYD per night
Guest favorite

Home in Westerly

4.96 out of 5 average rating, 48 reviews

Ocean front The Beach House

Sep 24 – Oct 1

G$180,266 GYD per night
Guest favorite

Home in Westerly

5.0 out of 5 average rating, 10 reviews

Watch Hill Beach & Pool Escape

Feb 20 – 27

G$205,061 GYD per night
Guest favorite

Home in Westerly

4.95 out of 5 average rating, 19 reviews

Minutes to the beach, pool, + beach pass! Westerly

Dec 13 – 20

G$97,057 GYD per night

Quick stats about vacation rentals in Watch Hill, Westerly

Total rentals

10 properties

Popular amenities

Beachfront, Gym, and BBQ grill

Wifi availability

10 properties include access to wifi

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

110 reviews

Nightly prices starting at

G$56,534 GYD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Rhode Island
  4. Washington County
  5. Westerly
  6. Watch Hill