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Check prices for these dates

Next weekend
14 Saf. - 16 Saf.
In two weeks
21 Saf. - 23 Saf.
In one month
7 Rab. I - 9 Rab. I
In two months
4 Rab. II - 6 Rab. II

Compare 153 Vacation Homes in Callaway with updated reviews, rates, and availability.

Screened Patio, Deck & Grill: Saint Inigoes Home!
Saint Inigoes Vacation Rental | 3BR | 2BA | 3 Steps to Enter | 1,456 Sq Ft

Screened Patio, Deck & Grill: Saint Inigoes Home!

Screened Patio, Deck & Grill: Saint Inigoes Home!
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
The driveway allows for plenty of parking for guests!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.6 out of 10, Exceptional, (29)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Terrace/patio

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Sunrise on your private beach

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

10.0 out of 10, Exceptional, (17)
"Great stay, easy check-in/check-out, highly recommend"
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Lusby Vacation Rental | 4BR | 3BA | 1,872 Sq Ft | Stairs Required

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

9.8 out of 10, Exceptional, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Belle of the Chesapeake Bay
Beach

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (12)
"Our granddaughters live in the neighborhood and our youngest was having her first birthday! It was just my husband and myself, way more house than we needed but tons more comfortable than a hotel. The winter views of the Bay from the living room were awesome. I highly recommend you make a cup of coffee and watch the sunrise. A few surprises with the house itself, the most egregious for me was the fireplace pictured is not functional. The hosts have done a nice job with this house and are still...
Belle of the Chesapeake Bay
4-BR Unique Waterfront House - Your Perfect Escape
Exterior

4-BR Unique Waterfront House - Your Perfect Escape

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
The price is SAR 844
SAR 1,896 total
includes taxes & fees
4 Feb - 5 Feb
4-BR Unique Waterfront House - Your Perfect Escape
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Sunroom off the kitchen and living room with a magnificent view of the Chesapeake Bay

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (112)
"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
4BDRM River front house with Private Beach in Hollywood
Property grounds

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.6 out of 10, Exceptional, (5)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths
Ariel view of the house, dock and beautiful Chesapeake Bay.

Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths

9.0 out of 10, Wonderful, (14)
"My family enjoyed our stay over Thanksgiving. Three generations with different needs and the house accommodated us well."
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths
Bay Estate by AvantStay | Waterfront, Private Pond
Pier.

Bay Estate by AvantStay | Waterfront, Private Pond

10.0 out of 10, Exceptional, (1)
"Such a beautiful house, very nice for family or friends get together."
Bay Estate by AvantStay | Waterfront, Private Pond
Your private beach retreat in historic St. Mary's
Welcome to your private beach and pier!

Your private beach retreat in historic St. Mary's

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at this property. The house was in mint condition and had all the amenities we needed. Enjoyed the hot tub, kayaks, the fire pit, and the dock. Great place to spend a relaxing long weekend. "
Your private beach retreat in historic St. Mary's
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
Warm and Homey with Beautiful River Front Views

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

9.8 out of 10, Exceptional, (10)
"Awesome property/location/amenities/host! We enjoyed every nano-second of our stay, and that is due to the host/hostess and the property they maintain and provide in the best way possible. We couldn't have wished for a better experience and hope to visit again and again. If you are planning to visit Cobb Island, this is the property you want to be at. Every inquiry before arrival was responded to promptly, and upon arrival, we were amazed at how clean and well addressed all our needs were...
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Scotland Vacation Rental | 3BR | 2BA | Stairs Required | 1,644 Sq Ft

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (9)
"I loved this sweet A frame home! Celebrated my 48th birthday with a girls' trip and we all loved it. Enjoyed fires and Christmas movies each night. House has a lot of space and is so comfortable. Loved the views of the Bay, particularly from the sunroom and porch. Found quite a bit of sea glass on the neighborhood beach, as well as at the house beach during low tide. Owner was incredibly responsive and went above and beyond. Great place. Would highly recommend. "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Luxury Modern Waterfront Retreat
★ Coziness & Outdoor ★ Gas fire-pit to enjoy your evening or wood fire-pit if you prefer the wood crackling sounds

Luxury Modern Waterfront Retreat

9.8 out of 10, Exceptional, (10)
"Very nice inside, love all the windows"
The price is SAR 596
SAR 1,751 total
includes taxes & fees
4 Feb - 5 Feb
Luxury Modern Waterfront Retreat
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
Sit on the patio and enjoy your coffee in the morning.

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

9.8 out of 10, Exceptional, (19)
"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
Waterfront Lusby Escape w/ Fire Pit & Kayaks!
Lusby Vacation Rental | 4BR | 3BA | 3,720 Sq Ft | Stairs Required

Waterfront Lusby Escape w/ Fire Pit & Kayaks!

10.0 out of 10, Exceptional, (6)
"Our family was looking for a place to gather to visit our Aunt who lives in the area. Six of us stayed at the Waterfront Lusby home and hosted a dinner for our Aunt and cousins. There was plenty of space for our gathering in addition to the comfortable accommodations for our weekend stay. The neighbors were very friendly and welcoming."
Waterfront Lusby Escape w/ Fire Pit & Kayaks!
Cottage on the Bay
Exterior

Cottage on the Bay

9.8 out of 10, Exceptional, (6)
"Clean and accommodating host. Has many of the necessities for the home, including washer/dryer , soaps , trash bags , cleaning essentials , plates/bowls/cups, kitchen gadgets , and more. Home feels safe away from predator animals . Couple deers around. Bring insect repellent."
Cottage on the Bay
Secluded River Front Cottage
Property grounds

Secluded River Front Cottage

9.4 out of 10, Exceptional, (3)
"The home and property are exactly as advertised. I loved being five minutes away from Point Lookout, the sunset views, and the waterfront. "
Secluded River Front Cottage
Waterfront home, dock, pool, pickleball, dog-friendly, fireplaces, a/c, jacuzzi

Waterfront home, dock, pool, pickleball, dog-friendly, fireplaces, a/c, jacuzzi

2.0 star property
10.0 out of 10, Exceptional, (2)
Waterfront home, dock, pool, pickleball, dog-friendly, fireplaces, a/c, jacuzzi
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 Callaway

Soul Oasis - home on the Chesapeake Bay
Exterior

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (19)
"Beautiful place, very clean and nicely decorated. The only thing I wish was better was to have a bathroom upstairs and the stairs to be a bit easier to access, they are a bit tricky for those over 50:) nice view too!"
The price is SAR 484
SAR 1,069 total
includes taxes & fees
4 Feb - 5 Feb
Soul Oasis - home on the Chesapeake Bay
Cozy Cottage with access to and partially obstructed views of the bay.
Exterior

Cozy Cottage with access to and partially obstructed views of the bay.

9.6 out of 10, Exceptional, (17)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
The driveway allows for plenty of parking for guests!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.6 out of 10, Exceptional, (29)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
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.