See all properties

Winstead Inn

Property class: 4

Choose dates to view prices

Photo gallery for Winstead Inn

A two-story house with a well-lit front porch, a staircase leading to the entrance, and a garden with various plants and flowers. - Winstead Inn (Harwich)
A large, two-story house with a covered patio area, outdoor seating, and a stone waterfall feature. - Winstead Inn (Harwich)
A large swimming pool with a fountain, surrounded by lounge chairs and umbrellas, set against a stone building with multiple windows and a balcony. - Winstead Inn (Harwich)
A cozy living room with a fireplace, a Christmas tree, and festive decorations. - Winstead Inn (Harwich)
A corner building with a curved roof, large windows, and a well-maintained garden with various plants and flowers. - Winstead Inn (Harwich)
Located close to Harwich Port and Bank Street Beach, Winstead Inn provides free self-serve breakfast, a terrace, and a garden. This guesthouse is a great place to bask in the sun with a nearby private beach, sun loungers, and a free beach shuttle. Guests can also expect to find a fireplace in the lobby.

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Parking included
  • Air conditioning
  • Housekeeping

Off-peak, on budget: 30% or more off select hotels in our fall sale

Skip the crowds, keep the savings. AARP members save more after Labor Day. Book by Oct 7, 2026.

Room options

Available filters for rooms
Showing 11 of 11 rooms

View all photos for 2 Queen Beds, Fireplace

A bedroom with two beds, a ceiling fan, a television, and a fireplace.

2 Queen Beds, Fireplace

10.0 out of 10
Exceptional
(6 reviews)
  • 41 sq m
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Suite 2 Bedrooms, 2 Bathrooms

A bedroom with a bed, a desk with a lamp, a chair, a dresser, a ceiling fan, and a large window with curtains.

Suite 2 Bedrooms, 2 Bathrooms

  • 68 sq m
  • 2 bedrooms
  • Sleeps 6
  • 1 King Bed, 1 Queen Bed and 1 Queen Sofa Bed

View all photos for Suite

A cozy living room with a red sofa, a wooden coffee table, and a TV stand.

Suite

  • 56 sq m
  • Sleeps 5
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Captain Joshua Eldredge

A bedroom with a large bed, two bedside lamps, a wooden dresser, a chair, and a window with curtains.

Captain Joshua Eldredge

9.0 out of 10
Wonderful
(2 reviews)
  • 25 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Admiral's Suite

A bedroom with a four-poster bed, a wooden dresser, a bench, a vase of flowers, a fireplace, and a ceiling fan.

Admiral's Suite

  • 32 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed

View all photos for Mariner's Hideaway

A bedroom with a bed, two bedside tables, a ceiling fan, a window with curtains, and a door.

Mariner's Hideaway

8.0 out of 10
Very good
(1 review)
  • 21 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Chart Room

A bedroom with a wooden bed, a ceiling fan, a nightstand with a lamp, a chair, a dresser, and a rug.

Chart Room

8.0 out of 10
Very good
(1 review)
  • 27 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for Chandlery Port

A bedroom with a four-poster bed, a blue carpet, a wooden nightstand, a blue armchair, and a view of the outdoors through a window.

Chandlery Port

  • 33 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 Queen Bed and 1 Queen Sofa Bed

View all photos for Chandlery Starboard

A bedroom with a bed, two bedside lamps, a nightstand, a wall decoration, and a kitchenette with a microwave and a small fridge.

Chandlery Starboard

9.0 out of 10
Wonderful
(2 reviews)
  • 39 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for Exclusive Penthouse, 1 King Bed with Sofa bed

A bedroom with a large bed, a desk, a chair, and a ceiling fan.

Exclusive Penthouse, 1 King Bed with Sofa bed

10.0 out of 10
Exceptional
(1 review)
  • 63 sq m
  • Sleeps 4
  • 1 King Bed and 1 Queen Sofa Bed

View all photos for Premium Quadruple Room

A bedroom with two beds, a red sofa, a ceiling fan, and a dresser.

Premium Quadruple Room

10.0 out of 10
Exceptional
(1 review)
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

About the neighborhood

Located in Harwich, Winstead Inn is in the historical district and near a private beach. The area's natural beauty can be seen at Bank Street Beach and Nauset Beach, while Cape Cod Museum of Natural History and Cape Cod Museum of Art are cultural highlights. Don't miss out on a visit to Cape Cod Inflatable Park. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails nearby. Visit our Harwich travel guide
View more Guest Houses in Harwich
Map
116 Parallel, Harwich, MA, 02645

What's nearby

  • Lavender fields with tall purple flowers.
    Cape Cod Lavender Farm
    19 min walk - 1.0 mile
  • Brooks Academy Museum
    5 min walk - 0.3 miles
  • Cranberry Valley Golf Course
    3 min drive - 1.4 miles
  • Harwich Port
    4 min drive - 2.0 miles
  • Bank Street Beach
    5 min drive - 2.2 miles

Getting around

  • Hyannis Transportation Center
    29 min drive
  • Hyannis, MA (HYA-Barnstable Municipal)
    32 min drive

Restaurants

  • Cumberland Farms
    3 min drive
  • Dairy Queen
    4 min drive
  • Dunkin'
    2 min drive
  • Dunkin'
    4 min drive
  • Brax Landing Restaurant
    4 min drive

Similar properties

Indoor pool, outdoor pool
Freebird Motor Lodge by Reverie Boutique Collection
West Yarmouth
  • Pool
  • Hot tub
  • Parking included
  • Free WiFi
9.6 out of 10, Exceptional, 379 reviews
Freebird Motor Lodge by Reverie Boutique Collection
Compare similar properties

Property amenities

Parking and transportation

  • Free beach shuttle
  • Free self parking on site
  • Wheelchair-accessible parking available

Food and drink

  • Free self-serve breakfast available daily 8:00 AM to 10:30 AM

Things to do

  • Seasonal outdoor pool

Family friendly

  • In-room refrigerator
  • Seasonal outdoor pool

Conveniences

  • Limited-hour front desk

Guest services

  • Concierge services
  • Housekeeping (daily)
  • Porter/bellhop
  • Tour and ticket assistance

Outdoors

  • Beach loungers
  • Beach towels
  • Beach umbrellas
  • Direct access to a private beach
  • Garden
  • Pool loungers
  • Pool umbrellas
  • Terrace

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No elevator
  • Wheelchair-accessible parking
  • Wheelchair-accessible path of travel

More

  • 2 buildings
  • 3 floors
  • Fireplace in lobby
  • Mosquito nets
  • Smoking not allowed

Room amenities

Bedroom

  • Pillowtop mattress
  • Premium bedding

Bathroom

  • Free toiletries
  • Hair dryer
  • Towels provided

Entertainment

  • Flat-screen TV with cable channels

Food and drink

  • Refrigerator

More

  • Air conditioning (climate-controlled)
  • Ceiling fan
  • Free local calls
  • Phone

Policies

Check-in

Check-in start time: 3 PM; Check-in end time: 6:00 PM
Late check-in subject to availability
Minimum check-in age: 20

Check-out

Check-out before 11:00 AM
Late check-out subject to availability
Late check-out fee: USD 75

Special check-in instructions

The front desk is open daily from 8:00 AM - 7 PM
Guests will receive an email within 72 hours before arrival with check-in instructions; front desk staffed during limited hours
To make arrangements for check-in please contact the property at least 48 hours before arrival using the information on the booking confirmation
If you are planning to arrive after 3:00 PM please contact the property in advance using the information on the booking confirmation
For any questions, please contact the property using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools
Check-in for this property is based at 114 Parallel Street, Harwich, MA.

Access methods

Front desk (limited hours)

Pets

Pets not allowed

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Cribs (infant beds) are available for USD 35.0 per day

Property payment types

Important information

Optional extras

  • Late check-out fee: USD 75 (subject to availability)
  • Crib (infant bed) fee: USD 35.0 per day

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Tax ID - C0007521260
This property accepts credit cards; cash is not accepted
Safety features at this property include a fire extinguisher, a smoke detector, and a security system
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
Please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property

We should mention

This property does not have elevators
The seasonal pool will be open from May to October

Frequently asked questions

Does Winstead Inn have a pool?

Yes, this property has a seasonal outdoor pool.

Is Winstead Inn pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Self parking is free at this property.

What time is check-in at Winstead Inn?

Check-in start time: 3 PM; Check-in end time: 6:00 PM. Late check-in is available during limited hours.

What time is check-out at Winstead Inn?

Check-out is at 11:00 AM. Late check-out is available for USD 75 (subject to availability).

Where is Winstead Inn located?

Offering direct access to the beach, this Harwich guesthouse is in the historical district and within 2 mi (3 km) of Harwich Port and Bank Street Beach. Brewster Ladies' Library and Cape Cod Museum of Natural History are also within 9 mi (15 km).

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

Winstead Inn Reviews

9.4

Exceptional

9.8

Cleanliness

9.4

Location

9.6

Staff & service

9.4

Property conditions & facilities
Rating 10 - Excellent. 128 out of 155 reviews
Rating 8 - Good. 15 out of 155 reviews
Rating 6 - Okay. 7 out of 155 reviews
Rating 4 - Poor. 1 out of 155 reviews
Rating 2 - Terrible. 4 out of 155 reviews

Reviews

Verified review

8/10 Good

Erik

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great Location, Hotel was very clean and staff very nice.
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Gustavo

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I went with my family, including my two small girls. Room was clean, amenities were super nice, Staff was super friendly. And breakfast included in amazing. Definitely I Will return.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

KRISTEN

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great clean room, good breakfast and really helpful staff! Will be back.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Kristin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great property with beautiful pool area and option to use private beach at sister property. Dedicated parking space. Staff very nice and helpful. Continental breakfast included which is rare in this location. Centrally located, easy to travel to other areas on the Cape. Met several guests that return annually.
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities
Windstead Inn is a beautiful property!! Management was great, let us check in early and our room was upgraded. Would definitely stay again.
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

David

Liked: Cleanliness, staff & service, property conditions & facilities
Quiet, comfortable, breakfast included
Stayed 2 nights in Jun 2025
Verified review

10/10 Excellent

F Michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A wonderful property with a beautiful and quiet pool area and easy private beach access through its sister property.
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Eric

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I wasn’t sure how I felt about staying at this type of Inn, but apparently this is common for the area. I was pleasantly surprised, it was a beautiful property inside and out. A renovated 18th century property. The Inn was mostly connected, but I think it was three separate buildings. The side that I was on felt like entering a house and our room was off a large shared living area with one or two other rooms. The courtyard with the pool is gorgeous and relaxing. Not far from bars and restaurants and the beach is a short drive where you can use the beach patio of their sister property.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Piotr

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to stay at Cape Cod.Friendly staff.
Stayed 1 night in Sep 2023
Verified review

10/10 Excellent

Daniel

Liked: Cleanliness, staff & service, property conditions & facilities
The room was spacious and the shower was amazing!
Stayed 2 nights in Jun 2025
Verified review

10/10 Excellent

Susan

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

nice place

Very nice place..staff wonderful. Would stay there again.
Stayed 1 night in May 2024
Verified review

10/10 Excellent

Mary

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
This was a cute spot on the cape. Very charming. Great location too!
Stayed 1 night in Oct 2024
Verified review

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was great.
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

Frances

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

A place not to over look

Very quiet Inn. Beautifully kept, with many outdoor spaces to relax. The heated pool is a bonus
Stayed 1 night in Jun 2024
Verified review

10/10 Excellent

Renee

Liked: Cleanliness, amenities, property conditions & facilities
We recently stayed at the Inn for four nights in the Crow’s Nest, a beautiful and well appointed suite. The Inn is pristine and tastefully decorated. It is located in the beautiful and historic town of Harwich, very close to the ocean and many Cape Cod beaches. There are many fine restaurants close by, as well as quaint shops and lively taverns. Highly recommend!
Stayed 4 nights in Aug 2024
Verified review

8/10 Good

Anshuman

Liked: Cleanliness, staff & service
This is an antique hotel . They gave us free upgrade to a suite from single room. Hotel building is old but in excellent condition. They have nice pool as well. Breakfast have good options with some on demand specialty too. And their staff was so humble and supportive. Only con is that there is some smell in sofa bed upon opening which might be there due to non usage from long time. Overall great stay here
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Karen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Peaceful and beautiful property. Staff was wonderful.
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Julie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This stay was incredible. Very relaxing. The staff were outstanding. Breakfast was yummy each morning. The location was in a great spot to travel all around the Cape. The beach access at the sister hotel was incredible as well. Thank you Winstead Inn!
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Jonathan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved this place. Private beach area in particular. Charming inn feel.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Stacey

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff really went out of their way to make you feel comfortable. The room had everything you could want or need. The jacuzzi tub was a nice extra. Enjoyed the pool area.
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Kristi

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
very clean. friendly staff Aplus
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Jimmy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was a last minute find and it met all of our needs. It is in a convient location with their beach resort only a few minutes away, restaraunts close by etc. It is a small complex which is good not to much traffic and assigned parking that is close to your room. Breakfast came with the stay and the selection was more than what was expected.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Simone

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amazing stay at the beach house. Quiet and peaceful. Will definitely return.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Wendy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The decor was beautiful. Great bathroom. Good breakfast. Enjoyed the private beach. Very well located. Lovely place.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

James

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved our stay. Everything about the Winstead Inn was fantastic especially the staff who were extremely friendly and helpful. Shout out to Nicole who checked us in and made us feel welcomed and offered any assistance that we might need. No complaints at all except one suggestion. It would be helpful if coffee/tea was available more frequently than just between 7:15 and 10. Again, not a complaint, just a suggestion. We will definitely be returning!
Stayed 4 nights in Jul 2026