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.

Vacation Rentals in Trappe, MD and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    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}
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 24 Rentals in the Trappe Area
    loading...
    From
    $90
    / Night
    Payment Protection
    View Details
    1 / 32
    5 of 5 stars (2) Excellent
    Trappe
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    From
    $856
    / Night
    View Details
    1 / 29
    Trappe
    8 Bedrooms / 6 Bathrooms / Sleeps 16
    Overview Make Inquiry

    The following rentals are within 15 miles of Trappe, Talbot County, Maryland.

    From
    $375
    / Night
    Payment Protection
    View Details
    1 / 22
    5 of 5 stars (1) Excellent
    St. Michaels
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    From
    $125
    / Night
    Payment Protection
    View Details
    1 / 21
    Tilghman
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Get away and stay in our cozy cottage that sits on the Knapp's Narrows in Tilghman, MD. Captain's Watch is a Waterfront Cottage which has a screened porch with beautiful sunrise view of Knapps Narrows. It is nestled in a Working Watermens Village, 12 miles from Historic St. Michaels, Maryland on... View all property information
    Make Inquiry
    From
    $450
    / Night
    Payment Protection
    View Details
    1 / 18
    St. Michaels
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Cranford on the Miles is a waterfront home located on 3+ acres, in St. Michaels. Fully renovated, with Wi-Fi, there is a Master Bedroom with king bed, sitting room, and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and a Den with a trundle bed... View all property information
    Make Inquiry
    From
    $175
    / Night
    Payment Protection
    View Details
    1 / 20
    5 of 5 stars (3) Excellent
    Tilghman
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential street across from a marina... View all property information
    Make Inquiry
    From
    $450
    / Night
    Payment Protection
    View Details
    1 / 13
    5 of 5 stars (5) Excellent
    St. Michaels
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    travelers have booked this property
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Beautiful in town location! Just steps to shops, restaurants, winery, brewery, community pool, museums, boat ramp, and waterfront. This home has been renovated with amenities that will ensure a great time in St. Michaels. Home has three bedrooms; main floor master with a king and full bath,... View all property information
    Make Inquiry
    5 of 5 stars Reviewed September 9, 2014
    The home was absolutely beautiful. Right around the corner from the town. Perfect location! We had been to St. Michaels 3 times before this trip and now we finally found our...
    5 of 5 stars Reviewed August 19, 2014
    Very comfortable, well furnished and equipped house with both modern and historical features. We took advantage of the great location to walk to tourist sites, restaurants and...
    See all reviews
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 5
    3 of 5 stars (1) Average
    Cambridge, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Charming, historic home in the Neck District, Maryland's most beautiful, unspoiled area. This adorable east-facing 100-year-old home sits on a generous lot (over an acre) with forever waterviews, mature shade trees, flowering perennials, roses, large fenced vegetable garden, breezy patio, wide... View all property information
    Make Inquiry
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 12
    Easton
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Exclusive 2 bedroom upstairs waterfront apartment with private entrance located 20 minutes from historic Easton and St. Michaels and 30 minutes from Oxford. Enjoy the sunrise each morning on your own private deck overlooking one of the most peaceful and unique surroundings the Eastern Shore has to... View all property information
    Make Inquiry
    From
    $1,500
    / Night
    Payment Protection
    View Details
    1 / 7
    Oxford
    Studio / 4 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Secluded, tranquil home located on the water, between Easton and Oxford, Maryland. Includes five bedrooms, four bathrooms, fully equipped kitchen, sun porch, swimming pool and tennis courts. Grounds include private driveway, miles of walking paths, and dock with two kayaks. View all property information
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $759
    / Night
    Payment Protection
    View Details
    1 / 38
    St. Michaels
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Walk to the attractions of St. Michaels, MD, yet private and quiet on a point of land with 500' shoreline, Bay Cottage is your home on the Chesapeake Bay with a relaxing waterside pol, private harbor and pier, organic culinary gardens, fruit farm, wellness studio, and warm hospitalities. There are... View all property information
    Make Inquiry
    From
    $190
    / Night
    View Details
    1 / 13
    5 of 5 stars (1) Excellent
    St. Michaels
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    The historic and recently restored Thomas Blades House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, parks, restaurants, town pool, library, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor.... View all property information
    Make Inquiry
    5 of 5 stars Reviewed August 18, 2014
    Location location location! Walk to perhaps the cutest town ever! Friendly people ,dog loving community, sail boats, restaurants and such a lovely little town.. Perfection found!
    See all reviews
    From
    $350
    / Night
    View Details
    1 / 23
    5 of 5 stars (2) Excellent
    St. Michaels
    7 Bedrooms / 3 Bathrooms / Sleeps 11
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks, restaurants, churches, and... View all property information
    Make Inquiry
    5 of 5 stars Reviewed September 27, 2014
    Friends and family stayed at the home to watch my nephew get married on 9/20/14. I must say, the house was as much of the event as the wedding celebration. We went from 6 of us...
    5 of 5 stars Reviewed July 23, 2014
    Our daughter was married at the Tidewater Inn in Easton. We rented this lovely, large home the week before the wedding to have a place for the bride to relax while we spent time...
    See all reviews
    From
    $180
    / Night
    View Details
    1 / 20
    5 of 5 stars (12) Excellent
    St. Michaels
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Reviews (12) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    The recently restored historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, town pool, parks, restaurants, library, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor,... View all property information
    Make Inquiry
    5 of 5 stars Reviewed August 22, 2014
    The pictures of this house do not lie. It is that nice. We parked our car and didn't need again until we left. Close to everything. Walk to the water , sit on the bench and...
    5 of 5 stars Reviewed July 20, 2014
    We fully enjoyed our relaxing stay in the sleepy little town of St. Michaels, and would definitely return when given the chance. The location is perfect - within a one block walk...
    See all reviews
    From
    $1,100
    / Night
    View Details
    1 / 22
    5 of 5 stars (5) Excellent
    Cambridge, MD
    7 Bedrooms / 6 Bathrooms / Sleeps 28
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Experience the lavish surroundings of Captain's Quarters. Whether your pleasure is sailing, fishing, water sports, relaxing by the pool and jacuzzi or nestling up on the veranda with a good book, Captain's Quarter's provides luxury around every corner. This unrivaled waterfront estate accommodates... View all property information
    Make Inquiry
    5 of 5 stars Reviewed May 21, 2014
    I had my wedding at this property. The landlord, Frank, was very polite and easy going. He allowed for our dogs to stay for a low fee and was very good at returning calls. The...
    5 of 5 stars Reviewed August 3, 2012
    I would not change a single thing. Our family enjoyed the six day stay at this awesome place. The amenities were great, the location was central to other sights, and the...
    See all reviews
    From
    $1,200
    / Night
    View Details
    1 / 39
    5 of 5 stars (2) Excellent
    Cambridge, MD
    5 Bedrooms / 4 Bathrooms / Sleeps 18
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Swan Cove awaits your family vacation or group! It's also an ideal place for a most memorable wedding. This incredible, newly redesigned waterfront home with a private dock offers spectacular views with a large swimming pool, 4 kayaks, outdoor firepit (firewood is furnished), playground and a large... View all property information
    Make Inquiry
    From
    $449
    / Night
    View Details
    1 / 30
    4.5 of 5 stars (9) Very good
    Cambridge, MD
    6 Bedrooms / 5 Bathrooms / Sleeps 16
    Overview Reviews (9) Make Inquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Private Fishing...
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Fabulous, recently-built premier vacation home on 500 feet of Chesapeake waterfront. A gorgeous home; beach, dock, private pool, boats, bikes, porches & mile-wide view With 6 acres of property, wide water & sandy beaches, this private luxury vacation rental is minutes from Cambridge,... View all property information
    Make Inquiry
    4 of 5 stars Reviewed April 1, 2014
    We had a group of 9 women stay here for a crafting weekend. The house was perfect for us. We brought a few folding tables and were able to all be in the large open rooms together...
    3 of 5 stars Reviewed July 28, 2013
    Our family spent a week at Saddle Beach House on the Eastern Shore over 4th of July. Unfortunately it was not the vacation we were hoping for. We chose this property because of...
    See all reviews
    From
    $449
    / Night
    View Details
    1 / 27
    4.5 of 5 stars (11) Very good
    Cambridge, MD
    7 Bedrooms / 5 Bathrooms / Sleeps 18
    Overview Reviews (11) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    New premier waterfront vacation home - 6bed / 5bath home w/ beach & private pool. All of this on over 3 acres and +- 400 feet of stunning waterfront Near Cambridge Maryland, also Easton, St. Michaels and Oxford. The den also serves as an additional bdrm with full bath making it 7bdrms. Ideal... View all property information
    Make Inquiry
    5 of 5 stars Reviewed October 28, 2014
    The Ideal Family Vacation This summer, our family decided to try something different and rent a house on the eastern shore of Maryland. After spending a day reconnoitering a...
    4 of 5 stars Reviewed October 12, 2014
    Really excellent location by the water, and the pool adds additional options. House itself is large, and is great for 2-3 families with kids. We were a group of friends, which...
    See all reviews
    From
    $375
    / Night
    View Details
    1 / 9
    5 of 5 stars (1) Excellent
    Bozman
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Grill
    • Internet Access
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas... View all property information
    Make Inquiry
    From
    $665
    / Night
    View Details
    1 / 7
    5 of 5 stars (8) Excellent
    Bozman
    4 Bedrooms / 2 Bathrooms / Sleeps 13
    Overview Reviews (8) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch (2 queens, 1 double, daybed w/trundle, 5 twins) 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large... View all property information
    Make Inquiry
    Get the List
    From
    $500
    / Night
    View Details
    1 / 18
    5 of 5 stars (6) Excellent
    Cambridge, MD
    6 Bedrooms / 3 Bathrooms / Sleeps 18
    Overview Reviews (6) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    The Swan's Nest in Cambridge, Maryland, has all that the Chesapeake Bay has to offer: sun, sand, fishing, crabbing, a par 3 golf course on site and so much more. The spacious and lovingly restored farmhouse can accommodate 18 guests. The kitchen is fully equipped and a barbeque pit is just outside... View all property information
    Make Inquiry
    5 of 5 stars Reviewed October 7, 2014
    So enjoyed this beautiful farm house with all amenities. So pleasantly surprised that everything was just perfect. Did not want to expect what we normally expect when we travel...
    5 of 5 stars Reviewed September 20, 2014
    All 4 couples loved our stay, Hap was very cordial and gave us everything needed. The house was very comfortable with great rooms thru out. Kayaks and canoes and bikes were a...
    See all reviews
    From
    $710
    / Night
    View Details
    1 / 38
    4.5 of 5 stars (3) Very good
    Church Creek, MD
    3 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This charming waterfront cottage on 6.5 private acres sits among swans and eagles on Marylands beautiful Eastern Shore. This professionally decorated cottage is packed with modern ammenities and charm. Waterfront Pool, Dock with seating boat slip with and water and electric; 1 canoe and 3 two... View all property information
    Make Inquiry
    4 of 5 stars Reviewed September 11, 2012
    We had a wonderful vacation in this lovely, secluded home. It was spacious, and had lots of windows with a view of the water and the dock was nicely set up for fishing and...
    See all reviews
    From
    $190
    / Night
    View Details
    1 / 40
    Cambridge, MD
    3 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Hot Tub
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    'The Cottage' at Heron Cove is a cozy home situated on a scenic peninsula with water views from every window. Awake each morning to watch the sun glisten off the gentle waters. Explore ten acres of land and 1000 feet of shoreline. Relax on the wrap around screened in porch or soak in the 450 gallon... View all property information
    Make Inquiry
    From
    $280
    / Night
    View Details
    1 / 9
    St. Michaels
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that this charming vacation cottage promises a fun, relaxing getaway. With a 180 degree expanse of spectacular Oak Creek waterfront, the River House at Royal Oak is the pefect choice for year 'round... View all property information
    Make Inquiry