GRANDVIEW, which was once known as Grandview at Pleasure Point, is a private estate located on 5¼ acres of Maryland’s famed Eastern Shore and is just minutes away from the restaurants and boutiques of St. Michael’s and Easton. It is surrounded by 1300’ of waterfront and 1,000 acres of wild life preserve, Grandview is a natural for fishing, crabbing, boating, and waterfowl viewing, with cycling, golfing, and other recreational and family activities near by.
Ideally suited for year-round getaways. All of our guests may use the pool, which sits on the point enjoying a “Grandview” of the water, the two piers, offshore anchoring, for our guests' pleasure, and plenty of picnic tables and charcoal grills.
The main house has a remodeled kitchen can seat 5 at stools and 4 at bar stools from the porch side and opens to the dining room seating 10 comfortably. There are 4 charming bedrooms and a large wrap around enclosed porch. The beds are queens, twins, and a full. Both bathrooms have been remodeled newly and are quite attractive and current in design. The furnishings are a combination of family pieces, antiques, and reproductions creating a very inviting and comfortable environment. There is a large screen smart TV in the living room with cable and internet as well as a fireplace. It is a great room for watching sports, having a fire, and being with friends and family in the off season. The first floor screened in porch provides a lovely view of the water, the pool, the point as well as a place to sit comfortably or at a picnic table for crab pickers. There is plenty of room for grilling outdoors and entertaining both inside and out.
Other things you should know:
VRBO collects 6% tax for the state of Maryland. Talbot County Maryland wants 41/2% and I must collect it myself. Also we give you the opportunity to save some money by electing to bring your own sheets and towels. We provide pillows, comforters, mattress pads, blankets etc. If we supply sheets and towels as well, there is a laundry fee of $15.00 per person. If you bring your own, there is no charge. We found this was very helpful especially during COVID Keywords: House
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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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Bozman
Located in Bozman, this holiday home is in a rural area and on the waterfront. Neavitt Park and Perry Cabin Park reflect the area's natural beauty and area attractions include Chesapeake Bay Maritime Museum and Phillips Wharf Environmental Center. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Chesapeake Bay Maritime Museum - 18 min drive - 18.1 km
St. Michaels Winery - 19 min drive - 18.8 km
Saint Michaels Village - 20 min drive - 20.1 km
Getting around
Cambridge Station - 58 min drive
Easton, MD (ESN-Easton - Newnam) - 38 min drive
Restaurants
Stars - 18 min drive
The Crab Claw - 19 min drive
Carpenter Street Saloon - 18 min drive
Foxy's Harbor Grille - 19 min drive
t at The General Store - 26 min drive
Frequently asked questions
Does Grandview- Main House have a pool?
Yes, this property has an outdoor pool.
How much does it cost to stay at Grandview- Main House?
As of 3 Apr 2026, prices found for a 1-night stay for 2 adults at Grandview- Main House on 11 Apr 2026 start from AU$1,119, 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 Grandview- Main House pet-friendly?
No, pets are not allowed at this property.
How much is parking at Grandview- Main House?
On-site parking is available at the property.
What time is check-in at Grandview- Main House?
Check-in begins at 4:00 PM.
What time is check-out at Grandview- Main House?
Checkout is at 10:00 AM.
Where is Grandview- Main House located?
Situated on the waterfront, this holiday home is 0.9 mi (1.4 km) from Neavitt Park and within 9 miles (15 km) of Perry Cabin Park and CL Open Field. Saint Michaels Town Hall and Higgins Yacht Yard and Marina 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.
Thank you for being so communicative and so understanding. It is always a pleasure to have guests who are appreciative. Please do come again and make Grandview your destination place.
I booked this VRBO for a small group of friends and me. We had a friend's wedding in St. Michaels. The location has a beautiful view and plenty of space to spread out but also great locations to gather around with friends. I would stay again if I find myself back in the area.
Tyler G.
Stayed 2 nights in Apr 2025
Response from VrboOwner on 1 May 2025
Thank you so much for you comments. Thank you for leaving Grandview is such a good state. Love to have you again.
Cordially
Anne
View can’t be beat for sunrises, water on three sides! Everything you need for family event in the kitchen, beds were clean and comfortable. Plenty of parking and trash cans. Could not ask for more!
Benjamin W.
Stayed 4 nights in Nov 2023
Response from VrboOwner on 28 Nov 2023
I have found Ben to be reasonable and cooperative. He understands how difficult it is to manage a place like Grandview and how special it is. That is a special quality from an owner's point of view.
Ann’s home is amazing. The view is unbeatable. We had a wonderful family trip with many great memories. There is so much outside space for the kids to run. It was perfect.
Kristen N.
Stayed 7 nights in Jun 2022
Response from VrboOwner on 7 Sept 2023
Thak you so much. We want Grandview to be a place for families and family memories. Please do come back.
Anne
The views at Grandview were beautiful. It was a quiet peaceful get away. Loved the wrap around screened in porches and pool. The kitchen is updated and while it is a very charming older home, some of the space could use a little refreshing.
Lynne & John R.
Stayed 10 nights in Jun 2023
Response from VrboOwner on 7 Sept 2023
Thank you for visiting us. I am always updating and wish I could do it all at once. I just spent $65000 on the porch plus more for the pool , grounds, dock. Etc. it never ends but we love to share what we have. And we will continue to get more things up to date.
Ann was so helpful before our stay, asking what our family needed to make everything accessible / comfortable ahead of check-in. We enjoyed the main level immensely, lounging around and spending time as a family. The kitchen had all of the supplies we needed to cook great meals.
The sunrise over the bay was incredible to watch from the dock. Really really enjoyed our stay!
Sierra D.
Stayed 3 nights in Nov 2021
Response from VrboOwner on 7 Sept 2023
It was a pleasure having you come to Grandview. We hope you will come back for another visit.
Cordially
Anne
We had a perfect stay at this gorgeous vintage home. Everything was beautiful. We cooked delicious meals in the fully stocked kitchen with room for all to gather, bedrooms were so comfortable, bathrooms gorgeous, watched the sunrise every morning and sunset every evening. Cannot say enough about how amazing this home is. We hope to come back in the summer and enjoy the pool and lovely grounds.
beth c.
Stayed 2 nights in Dec 2023
Response from VrboOwner on 11 Dec 2023
It is wonderful to have people that are kind and respectful and appreciative of what Grandview can share. Thank you and please do return!
Anne
Ann was great about communicating with us before our stay and the property was in such a beautiful location. We even did some family photos there that are now treasures. Ann was flexible too when plans changed for some extended family members. Thank you for sharing your home with us!
We rented both the main house and cottages for a get together with my extended family. The house was great and had plenty of room for a group. We also enjoyed the yard and being waterfront. We took the short drive into St. Michael’s one afternoon which was nice too. Overall everyone had a fun time and we would love to go back again.
Allison R.
Stayed 2 nights in Oct 2021
Response from VrboOwner on 7 Sept 2023
Thank you so much and you are more than welcome. Grandview is special!
Anne
The property was wonderful. Lots of room to enjoy celebrating my 50th with friends. It was exactly what I was hoping for! We enjoyed games at the large dining table and time in the outdoor space. The views are fantastic!
Melissa G.
Stayed 2 nights in Nov 2021
Response from VrboOwner on 7 Sept 2023
Thank you for choosing Grandview. We are so glad you had a nice time and hope you come back. We try to treat our guests like family. You are important to us.
Anne
We spent 4 days at Grandview and it was wonderful. The kitchen was perfect for big meals, the 2 grills were great, the pool so fun. The dock with 2 Adirondack chairs made for some cozy times with the young couples and for fishing early and late in the day. The beds were comfy and plentiful. The large dock was wonderful for all the fishing and crabbing.!Nice proximity to St Michaels and Tilghman Island
Family vacation with folks ages 13-55. Something for everyone to do. Very close to St. Michael’s and Tilghman island. Crabbing and fishing from the piers in the property. Pool and property are awesome. Very private.
Melissa N.
Stayed 7 nights in Jul 2022
Response from VrboOwner on 7 Sept 2023
Thank you so much! You were great guests and are welcome back!
Anne
This was the perfect spot for the seven of us to stay for a wedding at Maritime Museum. We enjoyed sitting outside, catching crabs, and picking crabs.
This VRBO had the best equipped kitchen! And we ended up cooking in more than had planned. Tommy, the property manager, was very helpful.
Andrea T.
Stayed 3 nights in Oct 2024
Response from VrboOwner on 14 Oct 2024
Thank you so much for your response. We are so glad you enjoyed yourself. We feel Grandview is very special and rejuvenating. Please do come again.
Cordially
Anne
As the pictures show, Grandview is located at the tip of a point with 2 sides on the water. House is old and quirky but with a modern, very well stocked kitchen. Bathrooms updated. It was a fun spot for our group. Enjoyed the pool on an unseasonably hot weekend in May.
Becky R.
Stayed 2 nights in May 2022
Response from VrboOwner on 7 Sept 2023
Thank you and please do come again. We are always repairing and updating so things do change!
Anne
Old house but clean. Host reached out on check in day. Great location. She had locals attending to yard and pool. They told us we could drop our boat in at a near by ramp and use the dock. Fire pit was nice. No wood but host told us where we could purchase from local stand. Gas grill available but no propane. 4 tanks at house were empty. We brought our own for crabs so we used that. Over all nice place and we would stay again
Richard H.
Stayed 3 nights in Sep 2025
Response from VrboOwner on 17 Sept 2025
Hello Richard, Yes, the house is old. It was built about 1890. We have updated more than you would believe and will be adding a new furnace and hopefully central air this fall and net spring. That of course means new power for the entire property It is never ending. I apologize for the empty containers. Everyone is supposed to be responsible for leaving a tank useable as opposed to empty. Obviously, that was missed. And I apologize. The local stand has great wood and just the right kind. We do not want people using logs and trees that have fallen down on our property. Too dangerous for a lot of reasons. And yes, you should provide your own crabs. Bur Tommy could have helped you get a good price as he knows everyone. You are more than welcome to come back. Then you can see the improvements we have made (hopefully). Love to have you. Cordially Anne
I came to Grandview with 4 of my friends for a girls’ getaway. We loved the historical details of the house and appreciated the modern appliances. The wraparound porch on both levels was amazing and there was plenty of room to spread out. Our favorite features were the large kitchen window that opened like a bar to the porch, and of course the amazing views! It was a short drive to St. Michael’s we hear we did a lot of fun shopping and dining. Overall highly recommend if you are looking for a beautiful getaway on the Bay!
Suzy K.
Stayed 2 nights in Oct 2022
Response from VrboOwner on 7 Sept 2023
Suzy was so cooperative and communicative. She left the house in great shape . I thank her and her friends very much!
Anne
We just finished a 2-week stay at the main house on the Grandview property — my wife, our teenaged son and 2 sets of friends who visited at different times. We had a blast. The pool was well kept and used every day. The house is charming and the 180-degree view of the water is relaxing. The owner, Anne Williams, was very responsive and helpful. St. Michaels is an easy, flat 10-mile bike ride from Grandview and we went nearly every day. Good time had by all and we will definitely rent here again!
John C.
Stayed 13 nights in Jun 2021
Response from VrboOwner on 7 Sept 2023
Thank you so very much. I am so glad you liked it! Please come again.
Anne
I stayed for my fortieth birthday with a group of friends and we could not have asked for a better home. It was BEAUTIFUL - clean, well-appointed, cozy, and absolutely perfect for a group of friends. The kitchen opens up to a lovely screen in porch, which was one of our favorite places to sit.
The property lives up to its name of Grandview because I could have sat and stared at that water for hours on end. We ended up renting kayaks (which I highly recommend) and it was the perfect setting to paddle around.
I can't say enough wonderful things about our stay. We are already talking about making this a yearly trip. Thank you for sharing your beautiful home!
Lindsay C.
Stayed 2 nights in Aug 2024
Response from VrboOwner on 4 Sept 2024
Thank you so much. It means a lot to have my guests happy. Grandview is very special to me.
And I would love to have you next year. Let me know what you are thinking. From June to Sept 1, the norm is week to week, Saturday to Saturday. I have people committed already for next summer so lets see what we can do for you.
Cordially
Anne
About the host
Hosted by Anne Williams
Why they chose this property
Because it is quiet, relaxing and spiritually rejuvenating
What makes this property unique
Peace, Comfort, and a great place for families or individuals to come and find one's self.