Vacation rentals with a patio in Oxford

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Top-rated accommodations with an outdoor patio in Oxford

Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

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Guest favourite

Apartment in Cambridge

4.92 out of 5 average rating, 101 reviews

Little Slice of Cambridge. Newly listed, 2 bedroom

You’ll be staying right in the center of the Historic district, close enough to walk to town and enjoy shopping or some of the great restaurants. Just two blocks from the water, a short stroll to the lighthouse or down to the water front and enjoy the park. This newly listed 2 bedroom , pet- friendly apartment has everything you will need to explore the history, food and waterfowl found in this area. Park your boat here. We can’t wait for you to experience Cambridge and relax in the “West End”.

Dec. 14 – 21

$226 CAD per night

Guest favourite

Cabin in Lusby

4.94 out of 5 average rating, 143 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a two bed, one bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish and catch crab --

Jul. 17 – 24

$502 CAD per night

Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 116 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

Jan. 2 – 9

$691 CAD per night

Guest favourite

Cottage in Oxford

5.0 out of 5 average rating, 17 reviews

Historic Home in Heart of Oxford, MD

Stay in a historic home built by the railroad when it came to town in 1880 (look for Pennsylvania Railroad memorabilia throughout the house!). Hardwood floors and fireplace with a yard on a quiet street, but in the heart of the historic bay town of Oxford, MD — half a block to the town market, coffee and ice cream, bookstore, and gift stores, and a block to the water on both sides of the house (enjoy beautiful sunrises & sunsets on the water!). Listed on the Natl. Registry of Historic Places.

Jun. 11 – 18

$356 CAD per night

Guest favourite

Guesthouse in Wye Mills

4.94 out of 5 average rating, 16 reviews

Adorable Lake Front 1BR Cottage-fully furnished!

This charming 1BR/ 1Bath cottage is located next to my primary residence. The cottage has its own private deck overlooking the Wye Mills Community Lake. The yard is spacious and pets are welcome. The yard is not closed in but safe for dogs who do not roam far. There is 1 queen size bed and queen pull out couch in the living room. Kitchen is equipped with basic appliances/ cooking and serving utensils and a full size washer and dryer. The bathroom has a stand up shower and basic necessities.

Jan. 10 – 17

$147 CAD per night

Guest favourite

Home in Saint Michaels

5.0 out of 5 average rating, 35 reviews

Shipwrights Cottage in Town!

Charming historic cottage within walking distance to all St. Michaels has to offer! Relax & enjoy the sights of town from your front porch! Once a working shipwrights cottage, this home is 2 stories with a 1st floor full kitchen, combo living-dining room, den with queensize pullout couch & full bath. The 2nd floor has 2 bedrooms & a full bath. Both bedrooms have vaulted ceilings & ceiling fans. The primary bedroom has a private sitting balcony. Walk to shops, restaurants & waterfront!

Mar. 18 – 25

$392 CAD per night

Guest favourite

Home in Greensboro

4.96 out of 5 average rating, 47 reviews

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

Apr. 14 – 21

$186 CAD per night

Guest favourite

Apartment in Saint Michaels

4.96 out of 5 average rating, 25 reviews

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

Nov. 7 – 14

$484 CAD per night

Guest favourite

Guesthouse in Oxford

4.9 out of 5 average rating, 21 reviews

Newly Renovated Guest House

Enjoy a delightful stay in a recently renovated, newly furnished guest cottage with water views in charming Oxford, Maryland. The house is in a quiet neighborhood with a beautiful view of Town Creek. Take a short walk or bike ride to town where you can enjoy fine dining and shopping. The house is equipped with TV, Wifi, AC to make your stay comfortable. There is reserved parking in front of the house and enjoy dining on the outside porch.

Feb. 18 – 25

$375 CAD per night

Guest favourite

Home in Cambridge

5.0 out of 5 average rating, 6 reviews

Magical Waterfront Home-Dock, Firepit, family fun!

Heron's Rest is a stunning home w/ magnificent water views, expansive patio, fire pit and dock - a peaceful place to gather with family and friends. Incredible location to explore the stunning and historic Eastern Shore and Historic Cambridge. Easy drive to the Atlantic beaches--you CAN have it all- boat, kayak, fish, birdwatch, explore Blackwater Wildlife Refuge, Easton, St. Michael's. There is a 3-night minimum from May 24 - Sept 02.

Sep. 22 – 29

$1,192 CAD per night

Superhost

Home in Cambridge

5.0 out of 5 average rating, 6 reviews

High St. Art Gallery Suite

This boutique suite is adjoined to the future home of High St. Art Gallery. This historic home was built in 1796 and is being lovingly restored by three generations of a family committed to creating beautiful, unique and comfortable spaces that can be a retreat away from home. This suite has all the details and delights that will make your stay enjoyable and we hope you will come again and again.

Nov. 17 – 24

$196 CAD per night

Guest favourite

Guesthouse in Annapolis

4.99 out of 5 average rating, 106 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Oct. 14 – 21

$622 CAD per night