Search Vacation Homes in Great Oak Landing

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Homes in Great Oak Landing

Luxury Waterfront Executive Family Home Annapolis with All Amenities

7.4 out of 10, Good, (3)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (50)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is AED 735
AED 1,114 total
includes taxes & fees
30 Sep - 1 Oct
BAYSIDE BUNGALOW

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (74)
"Great house, will stay again in the future. "
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (31)
"House was exactly as advertised. Quite community. Close to shopping, dining and beach! "
Entire Townhouse in Rock Hall

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (193)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

John’s Hopkins Downtown free parking 3 bedroom 3 bth sleeps 8 rooftop deck

9.4 out of 10, Exceptional, (3)
"We had a wonderful stay at Deanna’s house, everything was clean and easy to get in with self instructions. We liked that the house was also close enough to inner harbor. The owner had great communication too, thank you we’ll plan to stay again soon!! "
The price is AED 595
AED 1,705 total
includes taxes & fees
30 Sep - 1 Oct
John’s Hopkins Downtown free parking 3 bedroom 3 bth sleeps 8 rooftop deck

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (22)
"Peaceful relaxing getaway with my family. The cottage was perfect in every way. The property outside was a dream. Every day we were outside on the deck or dock enjoying nature. This is exactly what we needed to recharge with life. Can’t wait to come back and enjoy this perfect retreat again! "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

200 steps to the beach!

10.0 out of 10, Exceptional, (91)
"Good location "
200 steps to the beach!

Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler

9.8 out of 10, Exceptional, (23)
"Stunning property with tons of amenities for the teenagers to entertain themselves."
Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler

Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

10.0 out of 10, Exceptional, (19)
"Had everything we needed"
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

Want to get away? Staying with us. Very relaxing.

9.0 out of 10, Wonderful, (12)
"Loved the feel of the place! Was easy to unwind and was plenty big enough for our small family of 4! Getting to watch the sunrise and the wildlife off the back porch was surreal!"
Want to get away? Staying with us. Very relaxing.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (57)
"We had an awesome time at the property. The pool and jacuzzi are great for the family to play together. The house has board games and toys for the little ones, plus bikes to explore the little town. We will definitely be back. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.4 out of 10, Exceptional, (36)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA

Luxury Waterfront Home Built for Entertaining!

5.0 out of 10, (2)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
The price is AED 1,818
AED 3,052 total
includes taxes & fees
30 Sep - 1 Oct
Luxury Waterfront Home Built for Entertaining!

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.

Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

2.0 star property
8.6 out of 10, Excellent, (4)
"Would I stay here again? No. Would I recommend it to a friend? Also no.While the unit was clean, it felt quite tired and in need of a refresh. The kitchen was minimally equipped, with very few pots and pans, making it difficult to cook meals. Additionally, there were air fresheners and purifiers in every room, which made us wonder if they were masking an underlying issue. Overall, the space could benefit from some updates and better preparation for guests."
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (12)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

9.0 out of 10, Wonderful, (15)
"Our family of 11 stayed there for a week and absolutely loved it. Great views, large pool for the kids and a fishing dock for the fisherman in the family made it the perfect summer getaway. House is large and very clean and maintained."
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"This rental is amazing and highly recommended!! Beautiful decor! Very clean! Great outside hang out area! Awesome hosts!! Thank you so much for a great stay! "
The price is AED 724
AED 1,608 total
includes taxes & fees
30 Sep - 1 Oct
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Great Oak Landing Hotel Reviews