Search Cottages in Great Oak Landing

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 21 Cottages in Great Oak Landing with updated reviews, rates, and availability.

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (109)
"We were in town for the local triathlon and had a great stay! My kids (3&4) and I were able to walk to the finish line from the location. The house was clean and large enough that we were all comfortable. If you have kids, it’s across the street from a cool boat playground. Diane was very responsive to my questions and provided plenty of towels, blankets, etc. Overall, a great stay! "
Peaceful getaway convenient to local amenities including beach, boating & food

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (97)
"My wife and I, and our daughter's family (including our grandkids (ages 5 and 8) spent an amazing long weekend at Spring Cove Farm. We all loved our stay so much. The house was spotlessly clean and had everything we needed and the pier/water was gorgeous with ample kayaks and paddle boards. The kids fished from the pier for hours upon hours each day, and were thrilled at the selection of toys. Our daughter and son-in-law were working remotely and the Wi-Fi and Internet worked perfectlu. Dr....
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (133)
"Perfect location for watching the sunsets as the house is located right across the street from the beach. Also, an easy bike ride to restaurants and shops on Main St. The house is clean and comfortable. Highly recommend to other guests!"
Eastern Shore beach cottage get-away

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

10.0 out of 10, Exceptional, (7)
"Easy and flexible check in, clean and comfortable in a great location. Darling home. "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

House w/Water Views of Rock Creek 2BA 2BA Cottage

10.0 out of 10, Exceptional, (24)
"The house provided a clean, bright, spacious, well-equipped place for a family Thanksgiving gathering. It made for a very comfortable few days. The host was very responsive when we had questions before our stay."
House w/Water Views of Rock Creek 2BA 2BA Cottage

Be persuaded to experience this vintage cottage by the Sassa

9.4 out of 10, Exceptional, (8)
"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...
Be persuaded to experience this vintage cottage by the Sassa

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (1)
"Absolutely amazing place for my husband and I to relax with our midshipmen. Very clean, beautifully decorated and the view on the dock each morning was stunning! Close to restaurants (loved 3 B’s Bakery) and host was awesome! "
Rock Creek Cottage, Waterfront, Serene Views

Family-Friendly Cottage, Walk to the Beach!

10.0 out of 10, Exceptional, (18)
"Another amazing stay at Robin’s Rest. Highly recommend for a quiet weekend getaway "
Family-Friendly Cottage, Walk to the Beach!

Eastern Shore Getaway: Walk to Tolchester Marina!

3.0 star property
Eastern Shore Getaway: Walk to Tolchester Marina!

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is SAR 709
SAR 1,778 total
includes taxes & fees
14 Mar - 15 Mar
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Church Creek Cottage

Church Creek Cottage

Pet-friendly Home on Chester River w/ Dock!

3.0 star property
Pet-friendly Home on Chester River w/ Dock!

Rock Hall Retreat w/ Balcony Near Park & Marina!

3.0 star property
Rock Hall Retreat w/ Balcony Near Park & Marina!

Remodeled Abingdon House w/ Spacious Yard!

3.0 star property
Remodeled Abingdon House w/ Spacious Yard!

Waterfront Millington Vacation Rental w/ Hot Tub!

3.0 star property
Waterfront Millington Vacation Rental w/ Hot Tub!

Charming Edgemere Home w/ Deck & Grill!

3.0 star property
Charming Edgemere Home w/ Deck & Grill!

Family-friendly Cottage, Walk to the Beach!

3.0 star property
Family-friendly Cottage, Walk to the Beach!
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.
Don't see what you're looking for?
See all available properties in Great Oak Landing
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Great Oak Landing

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.

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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.

Frequently asked questions

Why book your cottage in Great Oak Landing with Expedia?
We think that a vacation should be easy, so if you’re looking for cottages in Great Oak Landing at an affordable price, Expedia has got your back. Keep the budget in check and stay in an economical option far from the downtown buzz, or splurge on a luxury cottage to spoil your favorite people.
How can I find cheap cottages in Great Oak Landing?
A good way to uncover cheap cottages in Great Oak Landing is with Expedia’s user-friendly filter tool. Narrow your search by star rating, amenities and budget to grab unbeatable rates in a couple of clicks.