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Watch Hill Holiday Rentals

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Our top choices for Watch Hill holiday rentals

1. Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Stonington
9.8 out of 10, Exceptional, (186 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

2. Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!

Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!
Westerly
9.0 out of 10, Wonderful, (16 reviews)
"Great spot, easy check-in and out, coffee, creamer, and sugar, snacks and water! Would recommend this for a 1/2 person stay! Great price!"
United States
Kelly A.
The price is NZ$310
includes taxes & fees
11 Sept - 12 Sept
Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!

3. A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!
Old Mystic
10.0 out of 10, Exceptional, (11 reviews)
"Absolutely adorable. Would stay again!!"
United States
Logan
The price is NZ$416
includes taxes & fees
15 Sept - 16 Sept
A Mystic Stay as Sweet as Apple Pie!

4. New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Old Mystic
10.0 out of 10, Exceptional, (46 reviews)
"This was a great place to stay. The property was beautiful and very peaceful. I would definitely recommend this property. It is very close to olde Mystic and downtown."
United States
Bonnie
The price is NZ$546
includes taxes & fees
1 Sept - 2 Sept
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

5. The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2

The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2
Stonington
10.0 out of 10, Exceptional, (9 reviews)
"Great stay with friends! "
United States
Danielle V.
The price is NZ$609
includes taxes & fees
9 Sept - 10 Sept
The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2

6. 1 Mile To Beach, 2BR, 1 BA, sleeps 6

1 Mile To Beach, 2BR, 1 BA, sleeps 6
Westerly
8.8 out of 10, Excellent, (177 reviews)
"Our host left a doggie bowl for our pups. The fridge was very clean. The neighborhood is lovely! "
United States
LiReesa W.
The price is NZ$855
includes taxes & fees
27 Aug - 28 Aug
1 Mile To Beach, 2BR, 1 BA, sleeps 6

7. Riverbed, Romantic Waterfront Suite, walk to town<br><br>

Riverbed, Romantic Waterfront Suite, walk to town<br><br>
Mystic River Historic District
9.8 out of 10, Exceptional, (49 reviews)
"Lovely, quaint, cozy, beautifully appointed and close to the heart of town."
United States
Maryann
The price is NZ$676
includes taxes & fees
8 Sept - 9 Sept
Riverbed, Romantic Waterfront Suite, walk to town<br><br>

8. 3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa

3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa
Westerly
9.8 out of 10, Exceptional, (28 reviews)
"The house was very clean and big it was perfect for a little getaway with friends"
United States
Anna F.
The price is NZ$1,673
includes taxes & fees
2 Sept - 3 Sept
3 BR Retreat 1 Mile to Westerly Beaches! 1 Bed King, 3 Queen Beds& Pull Out Sofa

9. The Blue Anchor House · walk Mystic-Train/Aquarium

The Blue Anchor House · walk Mystic-Train/Aquarium
Stonington
10.0 out of 10, Exceptional, (9 reviews)
"The house was clean, spacious and the location was perfect for all of our needs. Host was responsive when we reached out. Would definitely stay here again, and plan to in the future. "
United States
Bethany M.
The price is NZ$799
includes taxes & fees
8 Sept - 9 Sept
The Blue Anchor House · walk Mystic-Train/Aquarium

10. New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Old Mystic
10.0 out of 10, Exceptional, (39 reviews)
"Beautiful accomodations for our anniversary get away! Host was exceptional, friendly and the extra touches were special! Close to Mystic's great choices of restaurants and shops!"
United States
Dennis C.
The price is NZ$418
includes taxes & fees
9 Sept - 10 Sept
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

11. Upscale Apartment in Mystic 7 Minute Walk to Drawbridge

Upscale Apartment in Mystic 7 Minute Walk to Drawbridge
Stonington
10.0 out of 10, Exceptional, (34 reviews)
"Great location, quite area, walking to everything downtown highly recommended."
United States
Chad L.
The price is NZ$696
includes taxes & fees
27 Aug - 28 Aug
Upscale Apartment in Mystic 7 Minute Walk to Drawbridge

12. New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Old Mystic
10.0 out of 10, Exceptional, (14 reviews)
"Fantastic hosts and charming place to relax and recharge."
United States
Bryan C.
The price is NZ$455
includes taxes & fees
17 Aug - 18 Aug
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

13. Wilderness Camp

Wilderness Camp
Richmond
The price is NZ$164
includes taxes & fees
16 Aug - 17 Aug
Wilderness Camp

14. Lakeside cottage ON the water with beautiful views up the lake!

Lakeside cottage ON the water with beautiful views up the lake!
Ledyard
9.8 out of 10, Exceptional, (202 reviews)
"Sweet, cozy and clean. We had a nice time fishing, spotted a wide variety of birds, and enjoyed a few rounds of croquet. The lake was peaceful and quiet but is only a few minutes from the Foxwoods complex for shopping, dining, casino and shows. Thanks for a great stay!"
United States
Marcy P.
The price is NZ$733
includes taxes & fees
10 Sept - 11 Sept
Lakeside cottage ON the water with beautiful views up the lake!

15. Charming 3BR Apt 1 Mile From Downtown Westerly. Short Drive to Mystic & Casinos.

Charming 3BR Apt 1 Mile From Downtown Westerly. Short Drive to Mystic & Casinos.
Stonington
10.0 out of 10, Exceptional, (11 reviews)
"Great Stay! Niece than expected and great communication with Host! "
United States
Matt R.
The price is NZ$919
includes taxes & fees
16 Aug - 17 Aug
Charming 3BR Apt 1 Mile From Downtown Westerly. Short Drive to Mystic & Casinos.

16. "Shepherdess": Mystic Blue Salon With River View

"Shepherdess": Mystic Blue Salon With River View
Mystic River Historic District
9.8 out of 10, Exceptional, (17 reviews)
"Loved the location and communication we had with owner/staff. We would recommend having a TV in the apartment and a microwave. Other then that it was perfect."
United States
Elizabeth
The price is NZ$719
includes taxes & fees
14 Sept - 15 Sept
"Shepherdess": Mystic Blue Salon With River View

17. Beach Cottage 1 Mile From Weekapaug & Misquamicut

Beach Cottage 1 Mile From Weekapaug & Misquamicut
Westerly
8.8 out of 10, Excellent, (196 reviews)
"This place met all our needs. "
United States
Andrea G.
The price is NZ$1,186
includes taxes & fees
27 Aug - 28 Aug
Beach Cottage 1 Mile From Weekapaug & Misquamicut

18. Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Charming 1845 Home in the Heart of Mystic – Walk to Everything!
Mystic River Historic District
9.8 out of 10, Exceptional, (175 reviews)
"Great location "
United States
Brian S.
The price is NZ$690
includes taxes & fees
15 Sept - 16 Sept
Charming 1845 Home in the Heart of Mystic – Walk to Everything!

19. New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Old Mystic
10.0 out of 10, Exceptional, (23 reviews)
"Really really nice place. Big room very ornate decor."
United States
Steven M.
The price is NZ$473
includes taxes & fees
15 Sept - 16 Sept
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

20. Harbor View Landing, Mystic CT - The Cove Waterfront Cottage

Harbor View Landing, Mystic CT - The Cove Waterfront Cottage
West Mystic
9.8 out of 10, Exceptional, (18 reviews)
"We had a wonderful time at this cottage! It was extremely clean and very welcoming! It had everything we needed for an impromptu night away! The hostess was very responsive and accommodating. We would definitely stay here again! "
United States
Terri D.
The price is NZ$630
includes taxes & fees
24 Aug - 25 Aug
Harbor View Landing, Mystic CT - The Cove Waterfront Cottage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Watch Hill Hotel Reviews

Find out more about Watch Hill

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Watch Hill holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Watch Hill. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Watch Hill. Seeing all the best attractions is bound to make you fall in love with Watch Hill. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Watch Hill short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Watch Hill?

Yes, there are holiday rentals in Watch Hill close to The Flying Horse Carousel, or you can select a more secluded option if you're looking for a relaxing stay. Watch Hill is known for its beaches.

What are some of the best holiday rentals that Watch Hill has to offer?

Experience Paradise! Stunning Beachfront Home, Your Ultimate Coastal Retreat!: This holiday home rental outside of Watch Hill is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Watch Hill?

Expedia has 19 holiday rentals for your stay in Watch Hill.

What can I see and do in Watch Hill?

East Beach Watch Hill and Napatree Point are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Ninigret. While here, The Flying Horse Carousel and Misquamicut State Beach are other places worth a visit.

What’s a holiday rental in Watch Hill like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Watch Hill. Holiday rentals feature extras such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for small groups.