Search Vacation Homes in Great Oak Landing

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 150 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, (184)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
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, (53)
"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)
"Great location with a great view."
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, (13)
"Beautiful house, perfect for our family. The humans loved kayaking and bird watching on the river, the canine loved sitting out on the fenced in deck and relaxing in the nice cool AC"
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)
"The home was perfect for our family of 10. We spent most of our time on the beautiful screened in porch overlooking the river. The location was within a 5 min drive to all our favorite restaurants. The owners are very accommodating and quick to answer any questions. "
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)
"Very friendly and helpful host and a great property. "
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)
"The house is comfortable, clean and the location is fantastic. "
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 AED 893
AED 2,108 total
includes taxes & fees
28 May - 29 May
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, (33)
"Clean with comfortable beds!"
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)
"Wonderful place to 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 visited our son and fiancé for the week of Christmas and this place had everything we needed. Very clean, comfortable and the location was perfect. We want to stay here again on our next trip! "
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)
"A very nice and clean property to stay and rest. My daughter and I had a great time walking around Rock Hall and visiting the beach! A very nice neighborhood near downtown Rock Hall to go and see items of interest in the town but be able to go back to the property to rest and cook our meals. An excellent stay and visit!"
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)
"What a wonderful vacation we had everything you want is there. All you have to bring is food . The trampoline will keep everyone occupied for hours. Looking forward to staying there in the future."
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)
"Wonderful stay – Kids enjoyed fishing, floating in tubes and the hot tub! Very clean property with comfortable beds."
Beautiful, spacious, quiet waterfront house!
BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (35)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is AED 643
AED 997 total
includes taxes & fees
4 May - 5 May
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

BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (35)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is AED 643
AED 997 total
includes taxes & fees
4 May - 5 May
BAYSIDE BUNGALOW
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (47)
"We really enjoyed the water views & walking by the water. It was a very enjoyable and relaxing stay."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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, (184)
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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.