We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Callaway Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    C$246 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Callaway area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 20 Rentals in Callaway
    Sort by:
    Default
    The following rentals are within 30 kilometres of Callaway.
    Best kept secret by the bay (Entire House)1 / 20
    (4)Excellent
    Fishing Creek
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Old World Charm, Immaculate Potomac River Woodland Cottage, Polite Pets OK1 / 48
    (2)Excellent
    Piney Point
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Shannon Point Lodge Peaceful and Private1 / 17
    (49)Excellent
    Kinsale, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Parker Shores1 / 14
    (29)Very good
    Kinsale, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Waterfront
    • Cable/satellite TV
    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 18, 2018
    This place was amazing. Huge home with plenty of sleeping place. Good crabbing and fishing spot. The owner was awesome and provided us with any thing we needed along with advise...
    Reviewed June 23, 2016
    This is a good place. Plenty of sleeping room Three full bedrooms, several sofas downstairs, and a couple of extra cots downstairs. The kitchen was sufficient. The microwave...
    See all reviews
    About this property
    Great long-term rental for Locum Tenens, Hunting, Fishing Located in Westmoreland County at Sandy Point, VA, in the heart of Virginia's historic Northern Neck, approximately 2 hours from Washington, DC, 1.25 hours from Williamsburg and 1.5 hours from Richmond, VA. This fully furnished waterfront...
    View all property information
    Location Information
    Kinsale, Virginia 22488
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 11
    Make Enquiry
    Stunning Pond House in Coles Point1 / 32
    (1)Excellent
    Coles Point, VA
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Air Conditioning
    • Grill
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 15, 2016
    Myself and a few friends ending up spending a enjoyable weekend at this home. I would highly recommend it to anyone looking to get a away from it all for a few days.
    See all reviews
    About this property
    This vacation getaway is on a private lot on a 16 acre pond perfect for canoeing and kayaking, opening to the Potomac River. You are welcome to use our canoe and kayaks during your stay. The house sleeps 10 people in beds, two bedrooms are on the main level (one bedroom with a queen bed and one...
    View all property information
    Location Information
    Coles Point, Virginia 22469
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Chesapeake Bay Waterfront on Hoopers Island with Private Beach1 / 32
    (1)Very good
    Fishing Creek
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely home offers all the comforts of home, including a covered porch where you can meditate, read, paint, bird watch and get away from it all, as the quiet natural beauty of the area makes it the perfect retreat! The house features spectacular views of the bay and sunsets from the first...
    View all property information
    Location Information
    Fishing Creek, Maryland 21634
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    St George Island retreat, 1.3 hrs from Washington DC1 / 53
    (1)Excellent
    Piney Point
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Everything about the trip was perfect. The owner was very hospitable and provided everything we needed. Would rent again anytime!
    See all reviews
    About this property
    Experience luxury, peace, and tranquility when you stay at this superb 4-bedroom, 3.5-bathroom vacation rental house that sleeps 12 lucky guests on the Potomac River with unrivaled views of Potomac River. Situated on 10 acres of historic wooded land that lines the water, this house ensures amazing...
    View all property information
    Location Information
    Piney Point, Maryland 20674
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    Make Enquiry
    Lottsburg, VA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Air Conditioning
    • DVD Player
    • Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renovated waterfront house with small beach. Includes kitchen with all equipment, two bedrooms, one bathroom w shower, living room office space and two screened porches. Located in the historic Northern Neck region of Virginia. Enjoy crabbing, fishing, boating, kayaking, winery tours, and the...
    View all property information
    Location Information
    Lottsburg, Virginia 22511
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Fishing Creek
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Housekeeping Included
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious Historic Home. Wide open water views on both sides of the house! Come to discover 'Hoopers Hill'. Relax between waterfront sunrise and waterfront sunset. Gourmet kitchen, private beach, starry evening skies, and quiet reading spaces await. Shoreline crabbing, oystering and fishing too....
    View all property information
    Location Information
    Fishing Creek, Maryland 21634
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Cedar Beach Lodge is a Modern Year-Round1 / 8
    (2)Excellent
    Lusby
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Porch
    • Internet Access
    • Grill
    • Parking
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 28, 2018
    We rented this beautiful, well-kept and well-stocked lodge for a week-long family vacation. Deborah was excellent to work with and accommodating. The house offers plenty of...
    See all reviews
    About this property
    Cedar Beach Lodge is a modern, smoke free, year-round retreat located in the desirable and private Cove Point Beach Community on the western shore of the Chesapeake Bay. It is conveniently located 1 hour from Annapolis, MD and Washington, DC on Route 4 and 10 minutes from Solomon's Island, MD....
    View all property information
    Location Information
    Lusby, Calvert County 20657
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best Callaway rentals sent straight to your email!
    Get the List
    Hoopers Island Studio, 360 Degrees WATER VIEWS1 / 38
    (3)Excellent
    Fishing Creek
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 16, 2018
    Memories of the peace, beauty and comfort of Fishing Creek, Maryland and of the sparkling, colorful Queen Anne Cottage that is Hoopers Island Haven warm my cold winter days! If...
    Reviewed August 12, 2014
    We came to this historic area to do some fishing. The house was well equipped with emphasis to detail. A great deal of creativity is evident once you step inside. You find...
    See all reviews
    About this property
    360 Degree Views, WATERFRONT Scenic, peaceful and spacious studio apartment located on the entire second floor of our property. AVAILABLE FOR 2 NIGHT STAY MINIMUM, sorry NO EXCEPTIONS 3rd person $25 extra per night *Ironman/Eagleman/Event/Holiday: 3 Night minimum Discounted weekly rates....
    View all property information
    Location Information
    Fishing Creek, Maryland 21634
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Coltons Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy this beautiful, scenic and peaceful home on the Potomac River. Commune with nature and observe the wildlife, including deer and bald eagles. Go fishing from the pier. Eighteen private acres of natural forest and marshes. See the stars at night without the interference of city lights....
    View all property information
    Location Information
    Coltons Point, Maryland 20626
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    36486 Wild Rose Circle1 / 45
    (1)Excellent
    Piney Point
    5 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PET FRIENDLY* / 10% Military Discount** / View: Community / Sleeps: 15 / 5BR, 4BA single family homeAbout this home: This spacious 5-bedroom, 4-bath single family home - approximately 3,800 square feet - is a great place to relax and enjoy your vacation. This lovely home sleeps 15 people (and...
    View all property information
    Location Information
    Piney Point, Maryland 19975
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 15
    Make Enquiry
    New! Beachfront 4BR St. Leonard Cottage w/ Deck!1 / 24
    (1)Excellent
    Saint Leonard
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 29, 2017
    This amazing beach house has everything. The location and views are awesome. You literally step off the deck into the shells and sand onto your own beach and swimming area...
    See all reviews
    About this property
    Escape your everyday hustle and bustle and discover a hidden treasure right on the Chesapeake Bay sands at this 4-bedroom, 1-bathroom St. Leonard vacation rental cottage. With comfortable accommodations to sleep 8, 1,200 square feet of well-appointed living space and easy access to surrounding...
    View all property information
    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Waterfront
    • Internet Access
    • Parking
    • Outdoor Dining Area
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a peaceful beach getaway? Located in quiet Long Beach overlooking Flag Harbor Yacht Haven marina, this cottage is a few minutes walk to the sandy beach along cliffs famous for fossils from the Miocene. The shallow water is safe for children to swim, and a favorite for fishermen and...
    View all property information
    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Ridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Secure Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renovated & simply furnished cottage in a wooded setting with views of Saint Jerome's Creek, sunrises & sunsets from all sides. Rustic, open to the outdoors and water, this comfortable Southern Maryland Bay Home has an open space to the woods in the front, and to a pier overlooking Saint Jerome's...
    View all property information
    Location Information
    Ridge, Maryland 20680
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Broomes Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that the homeowner lives on site, in a completely separate unit with some shared outdoor amenities ** Enjoy an unforgettable getaway to this 1-bedroom, 1-bathroom vacation rental cottage overlooking Wells Cove! This serene St. Leonard residence, ideal for a romantic getaway for 2,...
    View all property information
    Location Information
    Broomes Island, Calvert County 20685
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Lusby
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you traveling for business or just for vacation? If so my one bedroom in-law suite w/ a large walk in closet, spacious living room, one full bathroom w/ access to a washer/dryer should be a perfect fit. For vacation 15-20mins from local waterfront restaurants/bars. Local attractions include...
    View all property information
    Location Information
    Lusby, Calvert County 20657
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Saint Leonard
    1 Bedroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Outdoor Dining Area
    • Internet Access
    • Grill
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax at this charming updated one bedroom bungalow. It overlooks the waters of Wells Cove, a tributary to the Patuxent River which is itself, a tributary to the Chesapeake Bay. This cottage is secluded from the main house, surrounded by water and a wild flower meadow. Somewhat secluded from...
    View all property information
    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 1 Bedroom, Sleeps 2
    Make Enquiry
    Fishing Creek
    7 Bedrooms, 3 Bathrooms, Sleeps 17 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The historic Queen Anne Victorian vacation rental home is the perfect, quiet respite for friends and family. With 7 bedrooms, 2.5 baths, and views of the Chesapeake Bay from almost every window, this scenic home is perfect for up to 17 guests looking to getaway. Updates and amenities provide...
    View all property information
    Location Information
    Fishing Creek, Maryland 21634
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 17
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    List your property
    Owner log in