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Check prices for these dates

Next weekend
18 Rab. II - 20 Rab. II
In two weeks
25 Rab. II - 27 Rab. II
In one month
9 Jum. I - 11 Jum. I
In two months
6 Jum. II - 8 Jum. II

Compare 148 Vacation Homes in Great Oak Landing with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (182)
"The house was beautiful and comfortable and had lots of incredible amenities. I stayed with a group of friends and their kids and it was so lovely being able to take them down to the water and make s'mores at the firepit at night. Highly recommend!"
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Miscellaneous

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Interior

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

10.0 out of 10, Exceptional, (47)
"Our stay was incredible! The house is beautiful, it is super spacious with tons of perfect places to congregate and hang out. The rooms were all extremely comfortable and the beds had high quality mattresses that made sleeping so enjoyable. The views and sunsets were spectacular and our group loved spending our evenings enjoying the hot tub. The house’s location is perfect as it is not only right on the water but it’s just under one mile from the (albeit super tiny) town of Rock Hall. I’d love...
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (12)
"I booked this house for a week as a quiet fishing trip get away. For starters Leone is awesome, always responds quick and is an amazing host.The house itself: was very clean, cozy, and had everything needed for a very comfortable stay. Other reviews said furniture was uncomfortable but I thought it was fine. Location was 3 min to foodlion, 10ish min to gas station, and about 16 min to large store for fishing gear. TV has netflix and lots of other shows to watch if thats what you want but most of...
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Beach

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

9.8 out of 10, Exceptional, (16)
"From the moment we entered the property the relaxation began!! The location and history of the area was interesting. The rooms were comfortable and homey. The screened porch was the central space and the reading knook was never empty. All enjoyed kayaking and paddle boarding in the calm river water. All agreed we would like to revisit the property again. Communication with the owners was prompt and courteous. Thank you"
The price is SAR 2,116
SAR 4,154 total
includes taxes & fees
24 Apr - 25 Apr
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Fridge, microwave, oven, stovetop

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (10)
"This house is very nice and conveniently close to Washington College. Teddi was responsive to our last minute rental. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Newly renovated single family home with attached guest suite
Smart TV

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (25)
"Owner/host was absolutely the best communicator. Spectacular views. The suite was an added bonus. Great beds in all the rooms . The kitchen provided great space to prepare family meals together. Wonderful water pressure. Stayed at the home for a special getaway for mom's 91st birthday. She kept stating "I love this little house". This home surpassed our expectations. This stay will forever have special memories. We hope to return. jold special memories "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Downtown home w/rooftop and free parking 3 bedroom 3 full bathrooms privacy deck
Exterior

Downtown home w/rooftop and free parking 3 bedroom 3 full bathrooms privacy deck

The price is SAR 912
SAR 2,194 total
includes taxes & fees
17 Apr - 18 Apr
Downtown home w/rooftop and free parking 3 bedroom 3 full bathrooms privacy deck
Waterfront family resort Lodge with private pier, game room and bar
Game room

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (25)
"We had a great time. Place was unique and good for group get together. "
Waterfront family resort Lodge with private pier, game room and bar
Waterfront Oasis w/ Private Dock, 3BR/2BA
Marina

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

9.4 out of 10, Exceptional, (32)
"Quick stay so I could visit family in Abingdon and DC. So awesome. Beautiful property even with the raging wind and snow storm."
Waterfront Oasis w/ Private Dock, 3BR/2BA
Amazing Waterfront Home on the Bush River
Terrace/patio

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at Ted’s property. The basement was cold as they hadn’t figured out to adjust the thermostat yet, so we didn’t spend any time down there. We also encountered challenges with the hot water heater, but overall it was a lovely stay. "
Amazing Waterfront Home on the Bush River
54 Mi to Dtwn DC: Spacious Family Home!
Fridge, microwave, stovetop, dishwasher

54 Mi to Dtwn DC: Spacious Family Home!

54 Mi to Dtwn DC: Spacious Family Home!
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Terrace/patio

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (76)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
CHeerful 3-bedroom waterfront home
Terrace/patio

CHeerful 3-bedroom waterfront home

10.0 out of 10, Exceptional, (35)
"We enjoyed exploring Baltimore - this was a great location for doing that! Could leave our dog without worry, nice area to walk her upon return. The house is perfect - super clean, suited us nicely with play space for toddler grandson and water view for g’parent coffee time!"
CHeerful 3-bedroom waterfront home
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Beach nearby, sun loungers, beach towels

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Lake

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

9.4 out of 10, Exceptional, (87)
"This was our 1st time in Maryland. We wanted a place on the water and that was able sleeps 8 adults and 5 children ages 5-16 comfortably. This home was perfect! The home was situated on the lake with a dock. It had 5 bedrooms (4 bedrooms with king size beds) and a sleeper in the living room area. Plenty of beach towels, fishing rods, access to canoe and kayak. Easy communication with owner and hassle free check-in. We would return and recommend this home to anyone looking for a relaxing...
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (2)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Beautiful, spacious, quiet waterfront house!
Fridge, microwave, oven, stovetop

Beautiful, spacious, quiet waterfront house!

10.0 out of 10, Exceptional, (47)
"Great view of the water, especially from the hot tub, staring straight out down the dock. "
Beautiful, spacious, quiet waterfront house!
BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (34)
"We had a wonderful weekend at Bayside Bungalow. Chris and Paul have really set up a great spot to enjoy some peace and quiet on the Chesapeake Bay. Thank you for your hospitality and attention to detail!Sincerely,J, J and L"
The price is SAR 657
SAR 1,003 total
includes taxes & fees
12 Apr - 13 Apr
BAYSIDE BUNGALOW
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.
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Other property types in Great Oak Landing

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

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

10.0 out of 10, Exceptional, (182)
"The house was beautiful and comfortable and had lots of incredible amenities. I stayed with a group of friends and their kids and it was so lovely being able to take them down to the water and make s'mores at the firepit at night. Highly recommend!"
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (80)
"The space was very clean. Communication with the owner was a breeze. It was quiet. The neighborhood is great. It is close to downtown Chestertown. A fabulous stay! "
The price is SAR 368
SAR 592 total
includes taxes & fees
6 May - 7 May
First Floor Studio Apartment in Historic Chestertown
Waterfront CHeerful 2 with Private Pier
Fridge, microwave, oven, stovetop

Waterfront CHeerful 2 with Private Pier

10.0 out of 10, Exceptional, (8)
"Quiet location on the water, well laid out. Very clean and very easy to work with. "
Waterfront CHeerful 2 with Private Pier
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.