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From179US$ /night
Check-in
10Jan2026Select date
Check-out
11Jan2026Select 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
4.8
/5

Rooms

The Cutty Sark offers a variety of room configurations to accommodate different needs. Guests can choose from rooms featuring one queen bed, two double beds, or combinations of queen and twin beds. Each room includes essential amenities like a flat screen TV, refrigerator, and microwave.

Location

Located just steps from the picturesque beaches of Dennisport, the hotel provides easy access to numerous local attractions. Guests can explore the nearby Cape Cod Museum of Natural History or enjoy a round at the Dennis Highland Golf Course, just seven miles away. For adventure seekers, Hyannis Whale Watching Cruises are available 13 miles from the hotel.

Dining

Several restaurants are within walking distance, making dining options readily accessible for guests. Enjoy a variety of cuisines from local favorites to casual dining only a short stroll away. The hotel's location encourages culinary exploration in the surrounding area.

Amenities

The Cutty Sark features an outdoor pool for guests looking to relax under the sun. Free parking is available on-site, adding convenience for those traveling with vehicles. Each room is equipped with a coffee maker, essential for starting the day.

Special Offerings

The hotel is particularly recognized for its easy access to local beaches, making it a choice destination for beachgoers. Guests can take in the coastal views just a hop across the street. The hotel's prime location enhances the beach experience for all visitors.

Highlights

Location: Steps from picturesque beaches

Room Types: Variety including queen and twin beds

Amenities: Outdoor pool for relaxation

Parking: Free parking on-site available

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 hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Economy Room One Double Bed
2 persons
15 m² 
1 Double bed
Heating
Air conditioning
Double Room Two Double Beds
2 persons
19 m² 
2 Double beds
Heating
Air conditioning
Queen Room
2 persons
19 m² 
1 King-size bed
Heating
Air conditioning
Queen Room Upper Level
2 persons
1 King-size bed
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Price and Room Availability Calendar

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Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

General

  • No smoking on site
  • Free Wi-Fi
  • 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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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
520 m
Beach
Raycroft Beach
520 m
Restaurants
Woolfies Bakery
980 m
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  ·  400 m
Airports
Barnstable Municipal -Boardman/Polando Field Airport (HYA)24 min  ·  16.0 km
Provincetown Municipal Airport (PVC)104 min  ·  69.3 km
Bus
Bus stop18 min  ·  1.5 km
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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
is available in 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
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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