The Cutty Sark Motel Dennisport Room photoThe Cutty Sark Motel Dennisport Beds photoThe Cutty Sark Motel Dennisport Room photo
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From179US$ /night
Check-in
20Apr2026Select date
Check-out
21Apr2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

396 Old Wharf Road, Dennisport, Massachusetts, United States, 02639
-
Near the beach
Great
8.6
9.6
/10
4.7
/5

Accommodations

The Cutty Sark offers diverse room options varying from economy to upper-level accommodations. Rooms include configurations such as one queen bed, two double beds, and one queen with one twin bed. Each room comes equipped with a refrigerator and microwave for added convenience.

Location

The hotel is situated steps away from the beautiful beaches of Dennisport. Nearby attractions include The Cape Cod Museum of Natural History and Dennis Highland Golf Course. Guests can easily access Hyannis Whale Watching Cruises, located just 13 miles away.

Outdoor Amenities

An outdoor pool invites guests to relax under the sun. The hotel also provides free parking as part of its amenities. Walking paths lead directly to the beach, accommodating beach lovers and sun-seekers.

Dining Options

Several restaurants are located within walking distance from the hotel, offering a variety of dining experiences. Guests can sample local cuisine and seafood specialties without needing to drive. This convenient location ensures a delightful culinary experience.

Family-Friendly Experience

The Cutty Sark welcomes families, providing rooms that accommodate various sizes and needs. Children will enjoy beach access and the outdoor pool area. The inviting location makes family outings to nearby attractions easy and enjoyable.

Highlights

Location: Steps away from beautiful beaches

Rooms: Configurations include one queen and one twin bed

Dining: Several restaurants within walking distance

Outdoor Amenities: Inviting outdoor pool

Must-do experiences

  • Visit the Dennisport Beach for stunning sunrise views.
  • Try the clam chowder at The Pure Cold Press for a local delight.
  • Stroll through the Cape Cod Lavender Farm for aromatic tranquility.
  • Explore the local artisan shops along Route 28 for unique finds.
  • Don't miss the historic Eastham Windmill, a beautiful landmark.
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Select your room type

The Cutty Sark Motel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Classic Room 1 Queen 1 Single Bed
2 persons
220 sq. feet 
1 King-size bed
Heating
Air conditioning
Economy Room One Double Bed
2 persons
165 sq. feet 
1 Double bed
Heating
Air conditioning
Double Room Two Double Beds
2 persons
205 sq. feet 
2 Double beds
Heating
Air conditioning
Queen Room
2 persons
205 sq. feet 
1 King-size bed
Heating
Air conditioning
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Price and Room Availability Calendar

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Facilities

The Cutty Sark Motel offers amenities for your comfortable stay and unforgettable experiences
Facilities: Great
8.6/10Review score

General

  • No smoking on site
  • Free parking
  • No pets allowed
  • Security
  • Fire extinguishers

Sports & Fitness

  • Hiking

Spa & Leisure

  • Outdoor swimming pool

Room features

  • Free Wi-Fi in rooms
  • Air conditioning
  • Garden furniture

Bathroom

  • Free toiletries

Media

  • Flat-screen TV
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The Cutty Sark Motel Location

396 Old Wharf Road, Dennisport, Massachusetts, United States, 02639
Map view
396 Old Wharf Road, Dennisport, Massachusetts, United States, 02639
Nearby
Beach
Sea Street Beach
1800 ft
Beach
Raycroft Beach
1800 ft
Restaurants
Woolfies Bakery
3300 ft
279 Lower County Rd
Explore Dennisport
Local Experience
Top Attractions
Activities
Dining
Entertainment
Sundae School Ice Cream
Sundae School Ice Cream
11 minutes' walk
A local favorite for handcrafted ice creams. Perfect for families with unique flavors and charming atmosphere.
Sea View Park
13 minutes' walk
Picturesque park featuring stunning ocean views and picnic areas. An ideal spot for relaxation and family outings.
Jericho House and Barn Museum
Jericho House and Barn Museum
10 minutes' drive
A historical museum offering insights into local culture and history. Guided tours available to enrich the experience.
Swan Pond
Swan Pond
10 minutes' drive
Tranquil nature area great for walking and birdwatching. Scenic views and peaceful surroundings make it a perfect retreat.
Kayaking at Bass River
10 minutes' drive
Thrill-seekers can rent kayaks for a fun day on the water, with rental services nearby for convenience.
Yoga at Pleasant Street Beach
10 minutes' drive
Relax and rejuvenate with sunset yoga classes on the beach. Seasonal classes available, ideal for mindfulness.
Cape Cod Rail Trail Biking
8 minutes' drive
Biking along scenic trails is a must. Rentals available nearby, making it accessible for all skill levels.
Woolfies Bakery
Woolfies Bakery
12 minutes' walk
Charming bakery known for fresh-baked goods. Enjoy coffee and pastries in a cozy setting, perfect for casual breakfasts.
The Potted Geranium
The Potted Geranium
5 minutes' drive
A delightful eatery featuring farm-to-table dishes. Known for its welcoming ambiance and seasonal menu, reservations recommended.
Harwich Cultural Center
Harwich Cultural Center
10 minutes' drive
Venue for art shows, live performances, and events. Family-friendly atmosphere with regular workshops and classes.
Cross Rip Gallery
Cross Rip Gallery
10 minutes' drive
Art gallery featuring local artists. Regular exhibitions and events provide a cultural outing for all ages.
Getting around
City Centre
Dennisport5 min  ·  1400 ft
Airports
Barnstable Municipal -Boardman/Polando Field (HYA)24 min  ·  9.9 mi
Nantucket Memorial (ACK)100 min  ·  41.4 mi
Bus
Bus stop18 min  ·  5000 ft
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Property information and rules
Check-in
from 15:00-23:59
Check-out
until 10 am
Guest Parking
Private parking is possible at a location nearby for free.
Internet
Wireless internet is available in the hotel rooms for free.
Children & extra beds
There are no cots provided in a room. 
Pets
Pets are not allowed.
Year renovated:
2011
Number of rooms:
14

Reviews and Ratings

Feedback about The Cutty Sark Motel from previous guests about their experience.
Review score
Based on 63 verified reviews
9.0/10
Perfect
94%
Recommend
Cleanliness
9.1/10
Comfort
8.8/10
Facilities
8.6/10
Free Wi-Fi
7.5/10
Location
9.4/10
Staff
9.4/10
Value for money
9.0/10
Guest reviews
based on 85 reviews
8.6/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
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FAQs
About The Cutty Sark
What is the check-in and check-out policy at The Cutty Sark?
Check-in is from 15:00 and check-out is by 10:00.
How far is The Cutty Sark from the nearest beach?
The hotel is just a 7-minute walk from Sea Street Beach.
What amenities are available in the rooms at The Cutty Sark?
Rooms include a microwave, refrigerator, flat-screen cable TV, en suite bathroom, and coffee maker.
What are some dining options near The Cutty Sark?
Nearby restaurants include The Ocean House (0.5 km) and The Ebb Tide (0.5 km).
Is there a pool available at The Cutty Sark?
Guests can enjoy a seasonal outdoor pool available from June 15.
What distance is The Cutty Sark from Barnstable Municipal -Boardman/Polando Field?
The hotel is 20 km from Barnstable Municipal -Boardman/Polando Field.
Does The Cutty Sark offer free Wi-Fi?
Yes, free Wi-Fi access is available in public areas.
What activities can guests enjoy at The Cutty Sark?
Guests can enjoy hiking and relaxing by the pool.
Is parking available at The Cutty Sark?
Free private parking is available on-site without a reservation.
What notable attractions are near The Cutty Sark?
Nearby attractions include the Cape Cod Museum of Natural History (14 km) and Hyannis Whale Watcher Cruises (21 km).
What payment methods does The Cutty Sark accept?
The hotel accepts Visa, Discover, and MasterCard.

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Rooms and Guests2 Guests, 1 Room