Cottage vacation rentals in Watch Hill, Westerly

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Top-rated cottage rentals in Watch Hill, Westerly

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

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Guest favorite

Cottage in Ledyard

4.91 out of 5 average rating, 109 reviews

Mystic, CT Pet-Friendly Cottage with Hiking Trails

Unwind at this peaceful, private Cottage with a fenced garden courtyard. Enjoy onsite hiking trails, EV chargers, an outdoor lounge, hammocks, firepit, lawn games, and a gas grill. Your stay includes organic breakfasts and eco-friendly amenities. Just 6 miles from Mystic, the Cottage is your dream escape. Book your stay now and create lasting memories with your pet! ❤️The Cottage books fast for weekends, holidays, & all of summer and fall. We recommend booking soon to guarantee your getaway.❤️

Guest favorite

Cottage in Oakland Beach

4.98 out of 5 average rating, 142 reviews

Renovated cottage w water views and walk to beach

This beautiful cottage has waterviews from most rooms. 1st floor has 4 season porch, Living room opens to white kitchen w quartz countertops, dining area , bedroom and 1/2 bath. 2nd floor has 2 bedrooms & full bath with laundry. Outdoor sitting at Small table in the front garden & Adirondack chairs in the backyard. 1/2 block to the beach, kayak, fishing, boat launch, cafe & 2 restaurants. Home has been renovated w love and caring. No parties. Please be considerate of cleaning person.

Top guest favorite

Cottage in Mystic

4.98 out of 5 average rating, 243 reviews

Mystic Cottage Retreat, near downtown

This recently renovated cottage is at the top of a quiet lane with a sweeping meadow view. Single level. Two bedrooms sleep four (queen and two twin beds); new, well-equipped kitchen and one bath, open living area, deck and patio. Light and spacious. Working fireplace, central A/C; W/D; expanded cable TV and wifi; off street parking for two cars. Market/deli nearby; pleasing walk (less than a mile from center of Mystic)- restaurants, shops, marinas, etc. Near Amtrak station. Great retreat!

Top guest favorite

Cottage in South Kingstown

4.94 out of 5 average rating, 125 reviews

The Snug Cottage: Walk to Water-Newly Renovated

Remodeled & simply adorable studio cottage. 216 sq.ft. New central AC & heat, kitchen w/ stove, oven, refrigerator, sink, & cabinets. Outfitted w/ plates, dishes & cookware. Eating area w/ drop leaf table. Comfortable, memory foam double bed w/ storage bins underneath. Bathroom w/ shower stall & pocket door. An outdoor shower for an easy post beach rinse too. Smoking not permitted in or on the premises. 2 parking spots on the property; NO BOATS/TRAILERS ALLOWED ON PROPERTY RE-01712-STR

Guest favorite

Cottage in Ledyard

4.89 out of 5 average rating, 195 reviews

Waterfront cottage overhanging the water!

Come relax at this cute and cozy cottage overhanging a large and beautiful lake! Whether it's a family trip, a couple's getaway, or a best friends reunion, this place has something for everyone. From relaxing on the deck with a beautiful view, to kayaking and canoeing, or swimming in the summer, there is much fun and peaceful relaxation to do at the cottage. Also, it's just a 10 minute drive to Mystic, wineries, orchards, the shoreline, restaurants, and 5 minutes to Foxwoods casino.

Superhost

Cottage in South Kingstown

4.88 out of 5 average rating, 112 reviews

2 BR East Matunuck cottage 7 min walk to beach!

Two bedroom cottage in The Village at Potter Pond fully equipped with appliances and Wi-Fi! 1/ 2 of a mile from East Matunuck State Beach, this village is located in the center of everything. Go for a swim, kayak, paddle board or even quahog in the Salt Pond which is just a few steps away from your front door. Grab dinner directly across the street at Captain Jacks or the Matunuck Oyster Bar. Set up your chairs, relax with friends / family & fire up the grill.

Top guest favorite

Cottage in Portsmouth

4.96 out of 5 average rating, 117 reviews

Waterfront, Dog-Friendly Cottage on the Cove

The cutest cottage on the cutest cove. Whether you’re into rosé & summer sun, hot chocolates in winter, a week off or a weekend away, Cove Cottage has water front views and a new dock to help you relax, unwind and enjoy the best of Aquidneck Island. One hour from Boston, and just 25 minutes to Newport, you have endless possibilities for what to do. Take out the kayaks or paddle board around the cove, dine in Newport or explore all Rhode Island has to offer!

Guest favorite

Cottage in Montauk

4.87 out of 5 average rating, 100 reviews

Secluded 1Br cottage on the lake, close to Ditch

This is the best of Montauk living, right by the lake, close to Ditch, and with an incredible, lush front yard suitable for outside dining or having a couple friends over for dinner. Walk down to the lake to enjoy the sunset, or stroll over to the Crow's Nest for drinks or dinner. No need to drive, it's well within walking distance. Join the many that have experienced the magic of our cottage at South Lake.

Guest favorite

Cottage in Mystic

4.97 out of 5 average rating, 104 reviews

Historic Mystic, CT - Harbor View Landing - The Cove Waterfront Cottage

The Cove unit is a queen-sized studio, waterfront cottage, with custom tiled private bathroom. This cottage comes equipped with retro mini-fridge, microwave, Nepresso coffee maker, HD TV, Amazon smart speaker, free wi-fi as well as a complimentary bottle of wine and water. Matouk linens and luxury Molton Brown bath products. Beach towels provided for complimentary water activities.

Superhost

Cottage in Sag Harbor

4.87 out of 5 average rating, 102 reviews

Secluded Hamptons Cottage

This cottage has high ceilings, is bright and airy, has a wrap around deck with a great overhang for hanging out in the shade or sun. You can not see a neighbor. It has been described as “an adult tree house.” Just a fun and relaxing place to be. It is on over an acre of rustic property. Perfect for watching wildlife.

Guest favorite

Cottage in Mystic

4.9 out of 5 average rating, 247 reviews

Cottage in downtown Mystic

Cozy 3 bedroom, 1.5 bath cottage in the heart of downtown Mystic. Walk to shops and dining, parks, the Mystic River and the Mystic Seaport. Aquarium and beaches nearby. Indoor areas light and airy. Plenty of outdoor space to enjoy with a deck, porch, and patio with a fire pit. Access to 2 kayaks.

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What guests are saying

Brady cottage, Little Compton, RI

4.97 out of 5 average rating, 63 reviews4 months ago

This is the second time I’ve stayed at Sheila’s cottage. It’s always a pleasant experience. Sheila is very responsive, and I’m highly satisfied with the cottage. It’s exactly as described, and everything worked flawlessly. I could not recommend this more highly.

Cottage in Little Compton

What guests are saying

Charming 3 bedroom cottage on Lake Pocotopaug

4.89 out of 5 average rating, 35 reviews7 months ago

The house was perfect. I felt right at home. Beautiful views. 5 min from town and my family. A view of East Hampton I have never seen. Host was easy to get a hold of. It was a home away from home. I plan to stay again if available when i need it.

Cottage in East Hampton

What guests are saying

Cheerful, private cottage in Essex village.

4.96 out of 5 average rating, 51 reviews6 months ago

This was the perfect place for my quick trip to Essex, CT. I was traveling alone and this little one bed/one bath was great for my needs. It was a little challenging to find at first, but once you figure it out, it's easy peasy - and I appreciated that it's set so far back off the street. The house is close enough to town that you can walk if you want to, and it's just an overall great location. I'll be back!

Cottage in Essex

What guests are saying

Seaside Cottage - Steps to Beach/Close to ferry

4.89 out of 5 average rating, 37 reviews7 months ago

We LOVED our stay! Sloane’s home was a perfect place for our sister getaway! The cottage was adorable and cozy! We enjoyed having coffee in the front room, relaxing on the back deck and slept great in the beds! The neighborhood was so quiet! Just a few folks walking their dogs! 🥰 We enjoyed walking on the beach, taking the ferry for a day trip to Martha’s Vineyard, eating supper & ice cream in New Bedford and did a quick day trip to Hyannis Port! This definitely checked off our ‘Cape Cod’ bucket list! Sloane was a great host with good recommendations and quick and friendly responses! Would definitely recommend her place for a quaint getaway!

Cottage in Fairhaven

What guests are saying

Game Room-Mins to Beach&Boardwalk-Walk to Marinas

5 out of 5 average rating, 15 reviews1 month ago

Erin’s place was perfect for our family weekend away! It was incredibly clean, stocked with everything we needed, and was a lovely space. The game room was a huge bonus, our son absolutely loved playing the arcade games all weekend :) Erin is a great host. Would definitely stay here again!

Cottage in Waterford

What guests are saying

Chic cottage on lush, secluded acre by the beach.

4.98 out of 5 average rating, 41 reviews2 months ago

We had a wonderful stay at Mischa’s home. The house was truly stunning - beautifully decorated and clean. Mischa has clearly thought about all of the little details that make a stay memorable - the kitchen was well stocked and the place was so cozy.

Cottage in East Hampton

What guests are saying

Remodeled Cottage Private Old Kelsey Point Beach

4.52 out of 5 average rating, 21 reviews8 months ago

Cheryl's place was adorable! I felt right at home in the cosy open concept living space. My mom crashed the weekend portion of the trip which was nice. My cat Mushu had a wonderful time and we even went outside. The beach was about a four minute walk for me, and a breathtaking view as you approach. Cheryl had everything necessary and mentioned. Next time I'll be sure to bring coffee filters and sugar. There were unexpected amenities too like paper towels and trash bags, and candles. There were also tons of spare toiletries like shaving cream and shampoo and conditioner and body wash. Thanks again!

Cottage in Westbrook