Guesthouse vacation rentals in Chesapeake and Ohio Canal

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Top-rated guesthouse rentals in Chesapeake and Ohio Canal

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Guest favorite

Guesthouse in Washington

4.9 out of 5 average rating, 411 reviews

Ingraham Alley Inn - A Quiet & Cozy Micro House

Our microhouse in 16th St Heights is the perfect home base for exploring the city. We're close to Rock Creek Park, the many restaurants and coffee shops of Petworth and Columbia Heights, and just a short bus ride from the downtown tourist sites. 16th St Heights is worthy of a little exploration in its own right, with a fantastic farmers market, beloved local eateries like Moreland’s Tavern and Highlands Café, and miles of forested bike/jogging trails in Rock Creek Park just a short walk away.

Nov 2 – 9

G$20,015 GYD per night

Guest favorite

Guesthouse in Washington

5.0 out of 5 average rating, 131 reviews

Gorgeous Two-Story Guesthouse w/ Free Parking

This spacious cottage is the perfect home base for families, couples, or professionals exploring DC. Start the day with breakfast made in a fully stocked chef's kitchen. Take a short walk to the Rhode Island Ave metro (Red Line), Catholic University, trendy Brookland restaurants, breweries, yoga studio, and grocery store. Rent a bike from Capital Bikeshare and hop on the nearby Metropolitan Bike Trail. At night, relax with a glass of wine around a cozy fire pit table on our cobblestone patio.

Dec 4 – 11

G$29,318 GYD per night

Guest favorite

Guesthouse in Falls Church

4.97 out of 5 average rating, 131 reviews

Beautiful New Apartment Surrounded by Nature

Beautiful, private detached studio apartment surrounded by a 3.5 acre park. Spacious light filled home away from home with a queen and single bed and available air mattress. Washer dryer in unit. Full private bath and kitchen with built in 2 burner induction burner, oven, microwave, coffee maker, hot pot, rice cooker and kitchen essentials. Walk to metro or take the bus from the corner. Bars, restaurants, grocery and other shopping and entertainment in walking distance or quick metro to DC.

Aug 20 – 27

G$22,973 GYD per night

Guest favorite

Guesthouse in Rockville

4.97 out of 5 average rating, 133 reviews

Modern Farmhouse Apartment. Close to Metro

Welcome to this beautiful and private 2 bed and 2 bath fully equipped apartment in a gorgeous modern farmhouse. Perfectly located in the City of Rockville. The apartment is in the basement of a newly constructed (2020) home. Completely separate with a private entrance and outdoor space. When you enter the home you will notice full natural light and high ceilings. No detail has been spared in the cozy 1000 sq ft apartment. From the full size laundry room to the soft close toilet seats.

Jun 19 – 26

G$42,157 GYD per night

Guest favorite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 645 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota guesthouse is the perfect get away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Nov 16 – 23

G$19,456 GYD per night

Guest favorite

Guesthouse in Arlington

4.94 out of 5 average rating, 139 reviews

Cozy Backyard Cottage in Historic Westover Village

Welcome to our Cozy Backyard Cottage! Studio style cottage located in quiet Westover Village neighborhood, just off Washington Blvd with great walkability. You'll be a 5 minute walk from The Italian Store, Lebanese Taverna, Westover Beer Garden & Market, Lost Dog Cafe, Toby's Ice Cream, Trade Roots and many more local small businesses. Ideal location for a business traveler or tourist couple looking for easy access to the DC and the surrounding metro area.

May 8 – 15

G$28,927 GYD per night

Guest favorite

Guesthouse in Highland

4.98 out of 5 average rating, 264 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool and adjacent walking trails.

Oct 18 – 25

G$24,973 GYD per night

Guest favorite

Guesthouse in Arlington

5.0 out of 5 average rating, 187 reviews

Private Sunny Cottage with King Bed + Yard / Patio

Welcome to Bagelot! Location! Location! Location! Nestled in the heart of Arlington, VA (extremely safe and ranked as one of the best cities for biking) -- just a quick car ride, moderate bike ride, or long walk into DC (Georgetown waterfront!) -- with spacious lawn and patio areas for lounging, grilling, sports, etc., this brand new cottage with high ceilings and lofted bedroom is the oasis within the city and home away from home you've been dreaming about!

Dec 2 – 9

G$58,914 GYD per night

Guest favorite

Guesthouse in Washington

4.96 out of 5 average rating, 157 reviews

Garden Suite

This light-filled, quiet and private apartment is an extension of the house, with a separate entrance, overlooking garden and pool, and a wooded area. The Unit has two rooms which are partially separated by a beautiful stone wall. The rooms offer every comfort needed for a stay, whether it is a weekend or longer. Cleveland Park is a historic neighborhood, boasting great restaurants, shops and lovely walks nearby, such as Rock Creek Park and the Zoo.

Oct 3 – 10

G$31,404 GYD per night

Guest favorite

Guesthouse in Warrenton

4.98 out of 5 average rating, 254 reviews

The Alton Cottage -a luxury country retreat

The Alton Cottage is a charming, newly refurbished 1820s guest house- formerly a summer kitchen to the original farm house. Views are of rolling fields and their bovine occupants. We are within 30 minutes of almost 20 wineries and another 20 breweries, 5 min to Airlie, and only 5 mi to Old Town Warrenton. We are also close to several antique stores, farmers markets and Shenandoah National Park. We strive to make every guests stay special.

May 28 – Jun 4

G$29,123 GYD per night

Guest favorite

Guesthouse in Rockville

4.92 out of 5 average rating, 301 reviews

Historic Carriage House with 1BR Loft

Historic 1-1/5 story carriage house in the heart of Rockville, MD. Located at the back of our property (detached from our main residence)- guest parking, private entrance, and covered outdoor patio with furniture available upon request. Modern but cozy decor. Comfortably sleeps 2 in king size bed, room for an additional guest on living room futon. Short 0.7 mile walk to Rockville Metro and Town Center.

Jul 19 – 26

G$27,552 GYD per night

Guest favorite

Guesthouse in Round Hill

4.98 out of 5 average rating, 376 reviews

Private Carriage House

A recently renovated carriage house by an interior designer situated on a treed and private property conveniently located for exploring wineries, breweries, horse events or civil war sites in Middleburg, Purcellville, Leesburg, Bluemont or Round HIill. Enjoy the sounds and sights of nature and fresh air. Recharge in a peaceful setting. Adults only. No pets, children or infants.

Jul 12 – 19

G$26,564 GYD per night