Holiday rentals in Watch Hill, Westerly

Guest house in North Stonington

4.98 out of 5 average rating, 188 reviews

"Mystic Country" Farm Stay at 100 Acre Wood

Let us welcome you to 100 Acre Wood, a historic farm and working cattle ranch. Owl's House is a private and stylish guest house nestled within the trees and garden and offers 180° views. Our farm store is stocked with our own TX Longhorn beef and pasture-raised chicken and eggs, plus curated with local products. Enjoy pastoral farm life and our private forest trails, or get out and play in the area's abundance of fine dining, wineries, seasonal attractions, outdoor activities, and entertainment.

4.98 out of 5 average rating, 374 reviews

Sweet Retreat Circa 1900 Restaurants, Park, Beach

Beautiful beach town 2nd floor self contained apartment in antique home! Perfectly located - a short walk to downtown cafes, park and 10 mins. to Westerly beaches. Quiet residential neighborhood. 3 bedroom apartment with ac & heat - kitchen, living room, bath and lovely porch. Mini splits & ceiling fans in BRs Zero contact entry. Family friendly! The first floor owner occupied. Close to casinos, Mystic, Newport, Prov. Stonington, Narragansett, URI and to the best beaches on the East Coast!

Superhost

4.88 out of 5 average rating, 126 reviews

Downtown Getaway Oasis 1 bedroom, 1 bath sleeps 4

Downtown 1 bd, 1 bth unit. Park your car and walk downtown to shop, grab a bite to eat, catch a movie at the renovated United Theater or take a stroll in beautiful Wilcox park. This gem is in the heart of Westerly and only a 10min. drive to the beach. Finish your day on the back porch overlooking the fenced in yard. Can sleep 4. 1 bdrm with Queen bed and living room pullout full size bed. Grocery, Liquor, restaurants, laundromat are all steps away from this well kept secret on a dead end road.

4.95 out of 5 average rating, 289 reviews

Flat in Stonington

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!

5 out of 5 average rating, 179 reviews

Home in Preston

New Lake Front Home w/ Game Room & Stunning Views

Relax and enjoy the breathtaking views of this new contemporary lake front home. Offering the best of New England, 7 min. from Foxwoods, 15 min. from Mohegan Sun, with multiple choices of hiking, boating, shopping and dining. Stunning 14' cathedral ceilings, fully equipped kitchen w/ granite counter tops, tiled shower w/ full amenities and a full game room. You can not get any closer to the water! This 1 Bdrm, w/ open low ceiling loft, sleeps 6, 1100 square ft. building completed in 2022.

Guest suite in Stonington

4.99 out of 5 average rating, 265 reviews

Morgan Suite - spacious | hot tub | water views!

The Morgan Suite is a private Airbnb located in a quiet neighborhood along the Pawcatuck River. Just minutes to downtown Westerly, downtown Mystic, beaches, breweries, wineries, shops, restaurants and much more. This Airbnb a perfect for a romantic getaway or a relaxing memorable vacation with a friend. If you are looking to explore a new area and relax, the Morgan Suite is for you! The home is spacious, newly renovated with excellent amenities. Newly added - hot tub and massage chair!

4.98 out of 5 average rating, 121 reviews

Guest suite in Westerly

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

4.96 out of 5 average rating, 142 reviews

Guest suite in Westerly

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.

Superhost

Apartment in Westerly

4.79 out of 5 average rating, 212 reviews

Cozy Condo.Walk to the Misquamicut Beach. Unit 1

Well-located in the center of the Misquamicut Beach, my place is excellent location for relaxing on the beach, bringing your bike, jogging, swimming, surfing, have a fun time at the beach. There are lots of restaurants and local bars in the area depends on your tastes and choices. Feel free to drive your car, ride your bike or walk to Watch Hill. Tasting Clam chowder in the very famous Ocean House may be one of the best choices. Options are endless.

4.98 out of 5 average rating, 125 reviews

Home in Westerly

Cheerful Cozy Colonial

Relax at this warm, welcoming peaceful place to stay, with hiking trails nearby and only 10 minutes to the beach and downtown Westerly. Set on 2+ acres, rejuvenate and connect with friends and family around the outdoor fire pit. Inside you will find a comfortable space with full kitchen, living room, dining room, three bedrooms and a full and half bath. In the warmer weather, enjoy the outdoor shower after a long hike or trip to the beach.

4.99 out of 5 average rating, 135 reviews

Home in Westerly

Cute and Close to Beaches and Town

A cute comfortable 2 bedroom 2 bath home with summer beach parking pass. Recently updated and furnished. A fenced in backyard. Allowing pets. Close to all in Westerly and South County. Grey Sail brewery, shops, restaurants. A 5 minute walk to restaurants, About a mile to Downtown Westerly and Wilcox park. 4 Miles to Misquamicut beach and Watch Hill. Central AC. Fenced in back yard allowing pets Great place to rent year round!

4.98 out of 5 average rating, 625 reviews

Guest house in Mystic

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodation and amenities

Popular amenities for Watch Hill, Westerly holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Watch Hill, Westerly

4.95 out of 5 average rating, 81 reviews

Cottage in Westerly

RI Perfect Misquamicut Beach Cottage Get-Away

PamRating, 5 stars8 months ago

This property is the perfect combination of privacy and public. A quick easy walk to the beaches/tourist area but since it's located on a quiet street, the space itself is very private. The home is beautifully maintained and quite comfortable. The hosts kindly provided coffee and bottled water, plus toiletry items that one of our guests had forgotten to bring. we would happily stay there again and love every minute of our visit.

4.94 out of 5 average rating, 17 reviews

Home in Stonington

Peaceful Beach Retreat/Casino Stay Alternative

MikeRating, 5 stars1 week ago

This place was perfect. So much to do locally and mystic is just a few miles away. would definitely stay again. GREAT HOST

Superhost

4.92 out of 5 average rating, 13 reviews

Entire 1-bed apt for relax & remote business trips

JayneRating, 5 stars3 days ago

Confusion checking in due to host being out of the country on vacation. Lovely apartment recently remodeled. Extremely clean and private.

4.99 out of 5 average rating, 77 reviews

Heathers On High Street King Bed/Twin Bed

KimberlyRating, 5 stars1 day ago

This was our first Airbnb stay and it was outstanding! Heather was so hospitable and the attention to detail was amazing! From the great communication to the thoughtful details of a personalized welcome card, to snacks, to ammenities she thought of everything, and I do mean everything! I work in customer service and it means alot when someone goes above and beyond for their guests. The cleanliness of the space was beyond my expectations, and I am picky! She was so kind and welcoming, we will definitely be back. We will be spoiled by this perfect experience, we just wish we had more time to enjoy the lovely back yard as well. Ammenities beyond compare should be the name of Heather's place! We will make up a reason to come to RI to stay here :-)

4.98 out of 5 average rating, 81 reviews

Tiny home in East Lyme

Lakefront Retreat Tiny House

MauriceRating, 5 stars1 week ago

Kevin is doing such a cool thing providing the perfect cozy escape with reasonable cost. Everything was as described and I can’t describe how relaxing and peaceful my stay was, especially considering it was actually a work trip in the area. He was always quick to respond to any needs I had & we had a nice chat after my checkout. Looking forward to hopefully being back in the area to stay at this exact spot again!

5 out of 5 average rating, 21 reviews

Home in Mystic

Mystic Harbor Retreat *Walk to River & Downtown*

ShannonRating, 5 stars1 day ago

I loved how organized Kathy was with her communication and sharing of information. I didn’t have to search for a thing. Everything went as expected (which rarely happens in the real world)! We were very pleased with our visit and the space she provided for us. It was clean, comfortable and the location was fantastic!

5 out of 5 average rating, 12 reviews

Home in North Fork

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

TimothyRating, 5 stars1 month ago

We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!