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Cottage vacation rentals in Westmoreland County

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Top-rated cottage rentals in Westmoreland County

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Cottage in Tall Timbers

4.9 out of 5 average rating, 106 reviews

Sunsets on Potomac, Woodland Cottage with Views

Southern Maryland at its best. Not on the water but across the street. Enjoy the fantastic sunsets slipping behind the Potomac River & Virginia. Situated in St Mary’s County near Piney Point and St George’s Island we are a short walk to Tall Timbers Marina, with its private museum, slips, docks, and homegrown oysters. Central heat & air conditioning, Auxiliary fireplace or front-yard fire-pit, Windows have screens. Fast Internet, WiFi, Smart TVs, Cable, Dogs w/approval, Plastic Kayacks

Nov 13 – 20

G$64,741 GYD per night

Cottage in Leonardtown

4.93 out of 5 average rating, 194 reviews

Potomac River Freedom Cottage

Welcome to the Freedom Cottage! We hope you will have a wonderful relaxing stay. Guest access will be provided via a keycode which will be emailed prior to arrival, spare key hanging inside. Guests will have access to the entire house and grounds (front and rear yard, stretching down to the beach/water). I won't be there for check-in/out but guests are encouraged to call/text during their stay if any questions arise. **Off-season long term rentals available, please contact me to discuss.

Sep 14 – 21

G$44,167 GYD per night

Cottage in Colonial Beach

4.83 out of 5 average rating, 142 reviews

SUPERB BEACH COTTAGE- Waterview, firepit, porch!

Dig your toes into the sand at Colonial Beach when you stay the 'Hummingbird Harbour,' a 3-bed, 2.5-bath cottage along the Potomac River! Ideally located only minutes from the shore, this quaint vacation rental is the perfect family getaway, complete with an expansive backyard, fire pit, and outdoor dining area. Take in the fresh ocean air from the screened porch with a steamy cup of joe in hand, or explore the shoreline with a walk down to Dockside Restaurant & Tiki Bar, found just steps away!

Jun 7 – 14

G$65,228 GYD per night

Cottage in Leonardtown

4.91 out of 5 average rating, 150 reviews

Potomac Vista Cottage at Little Pond

Charming 2 Bedroom 2 Bath located 20 ft from the Maryland Potomac Shore with expansive views across the river to Virginia! Relax to the sound of the waves breaking on the revetment. Easy Access to Historic St. Mary's City and Patuxent River Naval Air Station. The Potomac Vista Cottage, a perfect getaway from the stressed and fast paced city life, Has 1000 ft of living area furnished 2 Bedroom, 2 Bathroom, Great Room, Kitchenette, Laundry and a cozy deck with a beautiful view of the River.

Sep 20 – 27

G$33,129 GYD per night

Cottage in Kinsale

4.95 out of 5 average rating, 196 reviews

Great little cottage with a "Rivah" view

Welcome to our little slice of paradise on the Yecomoco river. This off the beaten path location has easy access into the Potomac for Rockfish or a little further into the Bay itself. Our dock can be used to swim, fish, crab or just relax and enjoy. A nice little marina is conveniently located nearby to put your boat into the river. Come and enjoy "Rivah" life at its finest. Unwind relax and enjoy. But if you do need to do a little work while you are here, we do have hi speed internet.

Oct 21 – 28

G$30,974 GYD per night

Cottage in Leonardtown

4.97 out of 5 average rating, 126 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Mar 21 – 28

G$37,745 GYD per night

Cottage in Colonial Beach

4.91 out of 5 average rating, 116 reviews

Shore Cottage Getaway - Water access

Enjoy relaxing at your cozy "Shore Cottage." Two bedroom one full bath cottage sleeps 4-6 people. Owners bedroom has queen size bed and Tv. Second bedroom has a Full size mattress bunk bed. Fully equipped kitchen and back deck grillin'! Enjoy relaxing on your front porch across from Monroe Bay. Walk to your private beach on the Potomac River. Also enjoy free access to your local marina on Doctor Point, where you can kayak, boat and even fish. Minutes from the winery, restaurants and parks!

Jun 7 – 14

G$47,334 GYD per night

Cottage in Colonial Beach

4.98 out of 5 average rating, 124 reviews

River view dog friendly YOLO Beach House

YOLO Beach House has a gorgeous sunrise view only one block to the river & blocks to the beach. Fenced yard excellent for children & dogs (dog door to back yard). Recently updated. Walking distance to Dockside, Castlewood park & the boat landing. Beach is pet friendly Oct to Mar only. The house & property are no smoking. Home has a whole home backup generator that does a self-check on Monday morning. It will start automatically if power is lost. We hope you enjoy YOLO as much as we do!

Oct 16 – 23

G$35,044 GYD per night

Cottage in Colonial Beach

4.94 out of 5 average rating, 68 reviews

Private home with dock

This vintage Colonial Beach cottage is the perfect getaway for all. Located on the point, it features private access to a deeded dock which is a 3-4 minute walk to the home. Enjoy laying on the hammocks in the front porch, or relaxing in the back porch while listening to your favorite vinyl records. The spacious back yard is perfect for entertaining, relaxing, or watching the kids enjoy the outdoors. There is also a golf cart which may be rented. Please message with questions.

Oct 21 – 28

G$37,576 GYD per night

Cottage in Colonial Beach

4.94 out of 5 average rating, 154 reviews

Bayside Cottage- In the Town with views

Welcome to Bayside Cottage, a newly renovated beach cottage in the very charming (Town of Colonial Beach), Virginia! The cottage boasts 3 bedrooms and 2 full baths and is centrally located in town. Walk across the property to Bayside Marina, where you can watch the sun go down on the rooftop deck with a drink in hand (contact host for instructions) Bayside Cottage was recently fully renovated and is best suited for groups of 6.

Jul 12 – 19

G$43,470 GYD per night

Cottage in Montross

4.94 out of 5 average rating, 17 reviews

Harbor Cottage

Nestled in a beautiful water community you'll find this modernized cottage. Harbor Cottage is a bright and open A-frame single family home, perfect for a quiet and cozy retreat. Relax on the four-season porch with panoramic views! Get outdoors and enjoy hiking, biking, bird watching or fossil hunting. A short 5 minute walk you'll find a sandy private beach perfect for sunbathing, shell collecting, fishing and stunning sunrises.

Oct 8 – 15

G$40,310 GYD per night

Cottage in Hague

5.0 out of 5 average rating, 83 reviews

Potomac River cheerful cottage

Embark on a journey to the serenity of nature and the gentle lullaby of the Potomac River at the cottage. Escape the hustle and let the timeless embrace of water and tranquility rejuvenate your mind and soul. The private sandy beach is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.

Dec 12 – 19

G$48,336 GYD per night

Vacation rentals for every style

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Popular amenities for Westmoreland County cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Reedville

4.91 out of 5 average rating, 143 reviews

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Nov 19 – 26

G$54,824 GYD per night

Cottage in Reedville

4.9 out of 5 average rating, 162 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

Dec 26 – Jan 2

G$138,040 GYD per night

Cottage in Saint Leonard

4.98 out of 5 average rating, 93 reviews

Hot Tub, Block to Beach, Fire Pit, Screened deck

Feb 3 – 10

G$58,483 GYD per night

Cottage in Scotland

4.93 out of 5 average rating, 15 reviews

Hays Beach House - Hot Tub - Private Beach

May 28 – Jun 4

G$197,762 GYD per night

Cottage in Heathsville

4.9 out of 5 average rating, 71 reviews

Waterfront Cottage w Private Beach & Hot Tub

Dec 2 – 9

G$46,275 GYD per night

Cottage in Montross

4.91 out of 5 average rating, 58 reviews

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

Mar 7 – 14

G$83,801 GYD per night

Cottage in Heathsville

4.89 out of 5 average rating, 18 reviews

Waterfront Heathsville Cottage w/ Dock & Hot Tub!

Jan 31 – Feb 7

G$70,662 GYD per night

Pet-friendly cottage rentals

Cottage in Montross

5.0 out of 5 average rating, 49 reviews

Paddler's Place: waterfront cottage with dock

Nov 20 – 27

G$48,118 GYD per night

Cottage in Leonardtown

4.85 out of 5 average rating, 65 reviews

Gorgeous Sunsets & Waves Heard from Bed. Why Wait?

Jul 25 – Aug 1

G$60,209 GYD per night

Cottage in Colonial Beach

4.9 out of 5 average rating, 48 reviews

Colonial Beach Cottage, 7 minutes walk to beach!

Oct 16 – 23

G$41,504 GYD per night

Cottage in Colonial Beach

4.94 out of 5 average rating, 82 reviews

Cottage Lafayette in Colonial Beach

Sep 8 – 15

G$44,784 GYD per night

Cottage in Colonial Beach

4.88 out of 5 average rating, 58 reviews

Bungalow Private Beach & Dock Colonial Beach Water

Dec 21 – 28

G$59,977 GYD per night

Cottage in Colonial Beach

4.94 out of 5 average rating, 64 reviews

Cozy Cottage w/ River Views & Front Porch Livin'

May 9 – 16

G$39,358 GYD per night

Cottage in Colonial Beach

4.91 out of 5 average rating, 32 reviews

Red Roof Cottage with sunrises from your porch

Sep 1 – 8

G$49,946 GYD per night

Cottage in Colonial Beach

5.0 out of 5 average rating, 24 reviews

Kokomo Cottage situated between the River and Bay

Nov 1 – 8

G$64,756 GYD per night

Private cottage rentals

Cottage in Leonardtown

4.95 out of 5 average rating, 57 reviews

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Sep 5 – 12

G$62,677 GYD per night

Cottage in Cobb Island

4.94 out of 5 average rating, 34 reviews

"Where Eagles Soar" Let magic and memories begin.

Sep 11 – 18

G$46,208 GYD per night

Cottage in Colonial Beach

5.0 out of 5 average rating, 19 reviews

Boaty McBeach House: Walk to Beach, Bay & Bites!

Sep 21 – 28

G$40,352 GYD per night

Cottage in Cobb Island

4.97 out of 5 average rating, 76 reviews

Happy Hour~Riverfront, countyside, private pier

Mar 1 – 8

G$45,015 GYD per night

Cottage in Colonial Beach

5.0 out of 5 average rating, 14 reviews

Resting Beach Face Charming River-View Cottage

Jun 1 – 8

G$40,649 GYD per night

Cottage in Tall Timbers

5.0 out of 5 average rating, 29 reviews

Charming Waterfront Cottage with Sunset Views

Feb 23 – Mar 2

G$98,920 GYD per night

Cottage in Kinsale

5.0 out of 5 average rating, 17 reviews

River + Beach Front Cottage 4 BR ADA Northern Neck

Dec 14 – 21

G$86,633 GYD per night

Cottage in Colonial Beach

4.97 out of 5 average rating, 90 reviews

Hawthorn Cottage Great In-town Location!

Feb 19 – 26

G$38,931 GYD per night

Destinations to explore