Holiday Rentals in Watch Hill

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Our top choices for Watch Hill holiday rentals

Aparthotel in Montauk

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1268)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is €151
includes taxes & fees
17 Dec - 18 Dec
Montauk Manor
10.0 out of 10, Exceptional, (4)
"We enjoyed our stay. The apartment is in excellent condition."
United States
Marcell
The price is €186
includes taxes & fees
4 Jan - 5 Jan 2026
Stevedore Landing-#3 · walk downtown Mystic · train · aquarium
10.0 out of 10, Exceptional, (14)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
The price is €254
includes taxes & fees
17 Dec - 18 Dec
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
9.8 out of 10, Exceptional, (191)
"There were stunning views, it was very relaxing, and we had excellent communication with the host. We couldn’t be happier, it was perfect! Kayaking was the best part. Plenty to see and do in the area as well."
United States
Heather S.
The price is €266
includes taxes & fees
4 Jan - 5 Jan 2026
Lakeside cottage ON the water with beautiful views up the lake!

Holiday Home in Old Mystic

A Mystic Stay as Sweet as Apple Pie!
2.0 star property
10.0 out of 10, Exceptional, (7)
"Loved the personal touches!"
United States
Jenny
The price is €186
includes taxes & fees
17 Dec - 18 Dec
A Mystic Stay as Sweet as Apple Pie!
9.8 out of 10, Exceptional, (16)
"Great property, beautiful grounds and appointed as described! Owners were great to work with and flexible. "
United States
Bill M.
The price is €225
includes taxes & fees
17 Dec - 18 Dec
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
10.0 out of 10, Exceptional, (5)
"Great stay with friends! "
United States
Danielle V.
The price is €202
includes taxes & fees
5 Jan - 6 Jan 2026
The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2
10.0 out of 10, Exceptional, (5)
"The cottage was beautifully decorated, cozy and made our stay very comfortable. The scenery was spectacular. We will definitely be going back!"
United States
Janet R.
The price is €282
includes taxes & fees
18 Dec - 19 Dec
Harbor View Landing Mystic, CT - The Nantucket Waterfront Cottage
9.8 out of 10, Exceptional, (218)
"Very comfortable, easy to get to and had everything you could need in a house rental! "
United States
Anna K.
The price is €253
includes taxes & fees
13 Jan - 14 Jan 2026
Lakeside cottage overhanging the water, beautiful window views across the lake
10.0 out of 10, Exceptional, (11)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is €316
includes taxes & fees
18 Dec - 19 Dec
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Mobile Home in East Lyme

Cozy Lakefront Tiny House
10.0 out of 10, Exceptional, (2)
"The bed and pillows were very comfortable. The outside space was very relaxing. Kevin’s place was perfect! We had questions and he replied back right away. We definitely want to go back. "
United States
Rebecca K.
The price is €198
includes taxes & fees
14 Jan - 15 Jan 2026
Cozy Lakefront Tiny House
10.0 out of 10, Exceptional, (33)
"Absolutely adorable! Beautiful view from our window. Quaint decor and every little detail thought of. Loved our stay! "
United States
Randolph
The price is €172
includes taxes & fees
17 Dec - 18 Dec
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
10.0 out of 10, Exceptional, (40)
"Great place to crash for a night when in town"
United States
Brendan H.
The price is €277
includes taxes & fees
17 Dec - 18 Dec
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
10.0 out of 10, Exceptional, (12)
"The Cottage was absolutely adorable and perfect for me my husband and our dog ❤️ Clean and cozy and the breakfast delivered to our door was amazing "
United States
Stephanie
The price is €234
includes taxes & fees
17 Dec - 18 Dec
Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!
10.0 out of 10, Exceptional, (126)
"We had an amazing stay at Merritt farm! The host was super accommodating and the house was perfect for our family. Hope has made sure the house has all the comforts of home and is decorated beautifully! The location is a great home base to explore this beautiful area. We would highly recommend staying here and we hope to return. "
United States
Robin G.
The price is €395
includes taxes & fees
17 Dec - 18 Dec
Unique Retreat w/ Private Patio, 4 King Beds & BBQ
9.8 out of 10, Exceptional, (158)
"Nice spot - about as close as you can get to the restaurants and shops downtown, but still quiet. "
United States
Bryan M.
The price is €206
includes taxes & fees
17 Dec - 18 Dec
Charming 1845 Home in the Heart of Mystic – Walk to Everything!
9.6 out of 10, Exceptional, (8)
"Super quick trip to get over to Mohegan for a basketball game."
United States
Brooke
The price is €246
includes taxes & fees
17 Dec - 18 Dec
Villa Noir- 3 min from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa
9.8 out of 10, Exceptional, (47)
"Small but clean and cozy! Not impressed just another apartment. Spa and pool very nice. I would return. "
United States
Johnny B.
The price is €220
includes taxes & fees
17 Dec - 18 Dec
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

Cottage in Breakwater Village

Cute cottage with a private beach
9.4 out of 10, Exceptional, (16)
"Close to the ocean, lovely area."
United States
Jackie C.
The price is €523
includes taxes & fees
22 Dec - 23 Dec
Cute cottage with a private beach
10.0 out of 10, Exceptional, (1)
"The home was very clean and welcoming."
United States
Michelle M.
The price is €322
includes taxes & fees
17 Dec - 18 Dec
Charming 2-bedroom house with WiFi, AC in lovely Waterford
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

Everything you need to know about Watch Hill holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Watch Hill holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Watch Hill holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Watch Hill holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Watch Hill. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Watch Hill holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Watch Hill holiday rentals we have selected for you start as low as €107 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Watch Hill rentals

At Expedia, we put the best Watch Hill holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Watch Hill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Watch Hill holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Watch Hill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Watch Hill?

Yes, there are holiday rentals in Watch Hill close to Ninigret, 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?

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages: This holiday home rental outside of Watch Hill has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Watch Hill?

Expedia has 15 holiday rentals for your stay in Watch Hill.

What can I see and do in Watch Hill?

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