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Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted

Photo gallery for Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted

A two-story house with a red roof, a covered porch, and a swimming pool.
A swimming pool with lounge chairs and a house in the background.
A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, a toaster, and a water dispenser.
A wooden deck with chairs and a table by a calm lake, surrounded by trees.
A dining area with a wooden table and chairs, a floral armchair, and a view through a glass door.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • On the beach
    A rare beachfront property in the area - enjoy direct access to the beach and sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • On beach
  • Balcony or patio
  • Massages in spa
  • Spa pool on site
  • Private pool
  • Dog-friendly

Explore the area

View map
Woolford, MD
  • Place, Blackwater National Wildlife Refuge
    ‪7 min drive‬
  • Place, Harriet Tubman Underground Railroad National Historical Park
    ‪18 min drive‬
  • Place, Northern Chesapeake Bay
    ‪21 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪59 min drive‬

Rooms & beds

7 bedrooms (sleeps 16)

3rd Floor Full's Bedroom

2 Double Beds

3rd Floor Twins Bedroom

+1
5 Single Beds

First Floor Den/Bdrm

1 Double Sofa Bed

Guest Room 2nd Floor

2 Single Beds

Guest Suite 2nd Floor

1 Queen Bed

Guest Suite 2nd Floor

1 Queen Bed

Master 2nd Floor

1 King Bed

5 bathrooms

3rd Floor Bath

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo

Ground Floor Bath

Soap · Towels provided · Bathtub or shower · Toilet · Shower only · Shampoo · Hair dryer

Guest Suite 1 Bath

Soap · Towels provided · Bathtub or shower · Toilet · Shower only · Shampoo · Hair dryer

Guest Suite 2 Bath

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Huge Master Bath

+1
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Jetted bathtub · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

Add dates for prices

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About the area

Woolford

Located in Woolford, this holiday home is in the city centre and on the beach. The area's natural beauty can be seen at Blackwater National Wildlife Refuge and Bill Burton Fishing Pier State Park, while Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center are cultural highlights. Travelling with kids? Consider Richardson Maritime Museum and Dorchester Arts Center. Jet skiing and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with hunting and horse riding nearby.
View more Holiday homes in WoolfordOpens in a new window
Map
Woolford, MD

What's nearby

  • Blackwater National Wildlife Refuge - 7 min drive - 6.5 km
  • Harriet Tubman State Park Visitors Center - 17 min drive - 17.8 km
  • Harriet Tubman Underground Railroad National Historical Park - 18 min drive - 18.4 km
  • Northern Chesapeake Bay - 21 min drive - 21.0 km
  • Choptank River Lighthouse - 22 min drive - 23.6 km

Getting around

  • Cambridge Station - 22 min drive
  • Easton, MD (ESN-Easton - Newnam) - 46 min drive

Restaurants

  • ‪Boats & Hose - ‬16 min drive
  • ‪Madison Bay - ‬8 min drive
  • ‪The Neck District Grill - ‬36 min drive
  • ‪Soft & Salty Seafood - ‬45 min drive
  • ‪Hudson Manor - ‬35 min drive

Frequently asked questions

Does Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?

As of 30 October 2026, prices found for a 1-night stay for 2 adults at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted on 25 April 2027 start from NZ$8,770, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much is parking at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?

On-site parking is available at the property.

What time is check-in at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?

Check-in begins at 4:00 PM.

What time is check-out at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted?

Checkout is at 10:30 AM.

Where is Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Dock Pet permitted located?

Located in Woolford, this beachfront holiday home is in the city centre and within 9 mi (15 km) of Blackwater National Wildlife Refuge, Christ Rock Park and Harriet Tubman Underground Railroad National Historical Park. Snows Turn Park and Bettys Island are also within 12 miles (20 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 72 out of 80 reviews
Rating 8 - Good. 7 out of 80 reviews
Rating 6 - Okay. 0 out of 80 reviews
Rating 4 - Poor. 0 out of 80 reviews
Rating 2 - Terrible. 1 out of 80 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
If you're looking for a relaxing getaway with quite surroundings and privacy, then this is the place for you. Property description in accurate. Owner is super helpful and laid back. Check in and check out policies are clearly listed and very reasonable, nothing out of the ordinary. FIVE stars across the board!!
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an absolutely wonderful stay at this vacation rental! The property was amazing, and we had everything we needed for a relaxing getaway. The views of the bay were incredible, especially at sunrise and sunset.Communication with the owner was excellent from start to finish, and check-in/out was simple and stress-free. This was easily one of the best vacation rentals we’ve stayed in, and we would absolutely return. Highly recommend to anyone looking for a relaxing spot with family and friends.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everyone enjoyed the pool, dock, beach,screened in porch. They have two refrigerators, bike helmets, toddler toilet seat, step stool on third floor. Bring room darkening shades for anyone who likes to sleep late. Two baby gates for the stairs were wonderful. Bring sand toys and water shoes for all. They provide many life jackets, pool and bath towels and wash rags. Bring bug spray since you are on the water! This was a wonderful family vacation for nine adults and five children under 7.5 years. We caught our own crabs and enjoyed 40 while we’re there! They have crab baskets and crab pots with crab mallets. Consider bringing black industrial trash bags to be on the safe side and newspaper to cover the table.Jon knows how to host and he is awesome at this! We hope to return!
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home is in a stunning location, and was perfect for our family gathering over the Thanksgiving holiday. Everything you need for a relaxing, enjoyable getaway is provided in this home, and we’d absolutely stay there again!
Stayed 5 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay!

We enjoyed our stay a great deal. Jon is a great host, the house was comfortable and spacious, and the view of the night sky from the pier was spectacular.
Stayed 7 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
As beautiful as the photos appear, they do NOT do this place justice! Just a beautiful place, incredibly peaceful, well-appointed and equipped for families, groups, or any type of rental. Loved our time here!
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family.
Stayed 7 nights in Aug 2025
Response from VrboOwner on 26 August 2025
We really enjoyed hosting you! So glad we could help with yor plans and your family's summer vacation! We look forward to having you back!
Verified review

10/10 Excellent

Liked: Check-in, communication, location, listing accuracy

Great Stay!

We had a great family and friends trip to Cambridge. The house was perfect and the communication with the owner was great. We hope to come back next year!!
Stayed 7 nights in Jun 2020
Response from VrboOwner on 27 July 2023
Kerry was a wonderful guest and we're so happy they had a great stay. We can't wait to have her, and her family back!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Sunshine, dolphins and campfire, oh my!

Great for families, and we have a big one. 8 adults and 7 kids (2 to 11 year olds) and plenty of room for all.
Stayed 4 nights in Apr 2023
Response from VrboOwner on 27 July 2023
Carol was just lovely to work with, they even brought two dogs and were well behaved! Seems like everybody in Carol’s party is a pleasure. She rented our seven bedroom waterfront home, and we would love to have her back.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

woolford

great property!
Stayed 7 nights in Aug 2023
Response from VrboOwner on 3 September 2023
Great guest!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Saddlebeach Property

Enjoyed this quiet, relaxing property along with the extras such as pool, canoes, and kayaks. The house is spacious and has plenty of conversation areas, as well as a beautiful view from many directions. It was a wonderful place for our family to vacation.
Stayed 7 nights in Jul 2020
Response from VrboOwner on 27 July 2023
Beth and her family were just, wonderful! We designed the property to be self-contained, while making it easy for our guests to make informed decisions and take advantage of all the area has to offer.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Weekend Getaway

What a beautiful property! We did a quick couples getaway and couldn’t have had a nicer weekend. The house is a beautiful, wraparound porch country home. Floorplan was really well designed and the decor was spot on. Looking forward to coming back next fall as well!
Stayed 2 nights in Dec 2023
Response from VrboOwner on 11 December 2023
Thank you Christine!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful setting and plenty of space

Jon is a super attentive host and his place is one of the nicest properties in the Woolford/Cambridge area. Kids caught crabs off the dock and enjoyed the canoes and kayaks Jon supplied. House had more than enough space for the adults and kids to all relax and eat together.
Stayed 7 nights in Aug 2022
Response from VrboOwner on 27 July 2023
Thanks! Love to have families enjoying everything the property has to offer. Evan and his family were exceptional to have at our home and we can't wait to have them back!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vacation on the bay

Perfect place for a secluded getaway with family and friends. Private pool, kayaks, canoes, bikes, fishing pier, and fire pit for marshmallow roasting! We had tons of fun! Jon was happy to help with anything we needed! We definitely plan to return!
Stayed 7 nights in Jul 2020
Response from VrboOwner on 27 July 2023
Lisa and her family were great guests! We're lucky to be able to share our property with so many nice families.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Christmas Holiday Family Getaway

Saddle Beach was roomy, well equipped and very comfortable for our Family Holiday getaway! We enjoyed card & board games by the indoor gas fireplace, and talks around the outdoor fire pit. Cornhole games, long walks/runs, and trips to the wildlife refuge and Tubman Museum filled out the week. Good times for all!
Stayed 11 nights in Dec 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Eastern Shore Respite

Wonderful weekend at this delightful property on the Eastern Shore. Quiet. Peaceful. Just perfect.
Stayed 3 nights in Jan 2023
Response from VrboOwner on 27 July 2023
Thanks Mark - he and his group were excellent to work with for their mid-January stay. We are a warm-weather paradise, yet we have a ton of families and friend groups that enjoy the property year-round. Lots to do here in colder months; from boating and biking to sightseeing and restaurant adventures. Mostly? Enjoying the home; cooking and spending quality time with friends.
Verified review

10/10 Excellent

Outstanding!

Jon was absolutely incredible to work with and rent from. This house is absolutely stunning. We enjoyed every aspect this house had to offer. Thank you Jon for sharing your home with us, we greatly enjoyed our time away.
Stayed 3 nights in Nov 2018
Response from VrboOwner on 27 July 2023
What a nice response - and this guest and their family+friends were wonderful. When you build a home that you love, and then share it with others? Their satisfaction is what makes it all worthwhile!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

80th Birthday Celebration

Just a wonderful property, with everything we could have asked for to help celebrate a wonderful occasion for our Mom. Both the actual accommodations, rooms, beds, baths, amenities, as well as the layout of the property were just great, whether we wanted to be together to celebrate, or spend quiet time reading a book, fishing, or just taking in the beautiful views! Several great gathering places inside and out, and we used them all! Would definitely recommend and hope to visit again!
Stayed 3 nights in Apr 2022
Response from VrboOwner on 27 July 2023
Thank you! Anthony and his family were wonderful guests. We designed the property to provide activities, entertaining and comfort for larger family groups and love it when others have fun at our home and property!
Verified review

10/10 Excellent

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

Great house for a large group

The house provided great accommodations for our large, extended family, and the pool and third floor were great for the grandchildren. It was a very hot week, so we understand the challenges for the AC, but we couldn’t get the main floor or the third floor cool.
Stayed 7 nights in Jul 2022
Response from VrboOwner on 27 July 2023
John was an exceptional guest! We SO wish they'd reached out about any cooling issues. We have three systems at the house and would have jumped at the chance to address it, and make them more comfortable. Even with the record heat wave that week.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely home, well-outfitted for a big group

We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we even found a restaurant on our side of the bridge that could seat all 16 of us for seafood. If you need a beautiful house in an equally lovely Eastern Shore setting, you will be happy with this one.
Stayed 4 nights in May 2025
Response from VrboOwner on 1 June 2025
We take great pride in providing a memorable stay with all the experiences for a family gathering. They're like so many of our generation family guests - looking for a great time on-property and off! Ron and his family were absolutely lovely to work with as well!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Saddlebeach

We absolutely enjoyed our stay at Saddlebeach. The house and grounds were everything we were hoping for and more. There were 15 of us- 10 adults and 5 kids ranging in age from 2 to 10. There was plenty of bedroom and bathroom space. The children were especially happy to have the pool to jump into and the dock to fish from. The list of restaurants Jon provided was very useful - we found Old Salty's which we really liked. We all had a wonderful time and are looking forward to coming back next summer
Stayed 7 nights in Jul 2023
Response from VrboOwner on 11 September 2023
Thanks Bill! You and your group were great, and took full advantage of all the home and area had to offer! Can't wait to have you back!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family, Fun, Fishing

Our family had a wonderful week in Woolford, MD. The house was just "as advertised" with room for games, lively conversations, and quiet reading. The dock was perfect for fishing and all our young people caught [and threw back] several fish. The kayaks and bikes were put to good use by everyone. Jon was friendly and answered our questions promptly. The house was well equipped with towels and kitchen supplies. Thank you for sharing your lovely home.
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Home, Breathtaking views, amazing host

We stayed at Jonathan's home for our multigenerational family reunion and Easter gathering. The home was incredible, with more than enough space to spread out for the adults and kids, and it had all the supplies and amenities we needed for family meals, daytime activities (from swimming in the pool to kayaking), and nightttime smores by the water. Jonathan was an incredible host. He was highly responsive, transparent, and worked with us to accomodate our particular needs. We will definitely stay here again in the future. Thank you for making this such a memorable experience!
Stayed 3 nights in Apr 2022
Response from VrboOwner on 27 July 2023
Thanks Charlotte for such a kind review and we're thrilled you had a great stay! Indeed making our guests happy is truly a pleasure for us :)
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Family Vacation

We couldn't have asked for a better vacation. The house was large enough to accommodate all 11 of us and had enough space that we didn't feel on top of each other. The kids loved the 3rd floor zone. The house was well equipped with everything we needed for a fun time. The dock was perfect for catching fish, crabs, and even rays. The kayaks were great for early morning or late afternoon rides. The pool was huge and allowed us to cool off. The host was very responsive to our questions. We enjoyed it so much we've already booked the house for next year.
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vacation paradise

A big, beautiful home with a well stocked kitchen, plenty of beds and space to gather! This home boasts a wrap around porch, a built in pool, a pond and a 240' dock over the Chesapeake bay! From the dock, we fished, crabbed and caught the morning sunrise! The canoes, kayaks and bicycles provided were well used and appreciated. We are 8 adults and 12 children ranging from 1 year to 14 years old. A memorable, fun time was had by all. Communicating with Jon was always a pleasure. Thank you for sharing this amazing home.
Stayed 7 nights in Jul 2024
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