Cabin vacation rentals in Chesapeake Bay

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Top-rated cabin rentals in Chesapeake Bay

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Guest favorite

Cabin in Lusby

4.94 out of 5 average rating, 146 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 20 – 27

G$67,899 GYD per night

Guest favorite

Cabin in Myersville

4.97 out of 5 average rating, 254 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Amazing place to unwind, de-stress & get away. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting.

Feb 11 – 18

G$23,639 GYD per night

Guest favorite

Cabin in Haymarket

4.93 out of 5 average rating, 199 reviews

Lodge on the Lake

A quiet 17 acre, ONE room cabin set on a private small lake, fishing, swimming, and kayaking. Equipped with a full kitchen, a grill, 4 OUT DOOR showers, no showers in cabin. Sleeps 4, 1 QUEEN SIZE BED AND 1 PULL OUT HIDE-ABED. There is a $25/PP per day for extra guests , with prior approval by host. Pet friendly. Cameras are on site. 1 at the parking lot, 1 on the side deck, back deck, covered porch, up stairs open covered card/chest room, 2 on the main dock & water, 1 outside stone pati

Nov 20 – 27

G$63,617 GYD per night

Guest favorite

Cabin in Chestertown

4.98 out of 5 average rating, 215 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

Oct 16 – 23

G$64,296 GYD per night

Guest favorite

Cabin in Lovettsville

4.97 out of 5 average rating, 120 reviews

Rustic cabin + modern luxury in Lovettsville

Enjoy a one-of-a-kind stay in this restored 1800s cabin guest house with modern updates and beautiful decor. Off the beaten track but only about 1 hour from both DC and Baltimore. Located on a working farmstead and close to wine country, breweries, a goat cheese creamery, farm-to-table dining, and more. A favorite landing place for those out in the country enjoying Loudoun's Artists' Tour, Farm Tour, Wine Country Half Marathon, a wedding, a hiking trip, or just a weekend in the countryside.

Oct 24 – 31

G$28,483 GYD per night

Guest favorite

Cabin in Lusby

4.91 out of 5 average rating, 211 reviews

Peaceful Waterfront Retreat on The Bay

This is a serene, waterside cabin with a private dock, nestled on quiet St. Leonard Creek about one hour outside of Washington, DC. You will enjoy a close quarters stay in this rustic studio cabin, and it is the perfect getaway for anyone looking for some peace and quiet. Come on your own to finally get some work done, or bring your family to enjoy the outdoors! We have two kayaks and two canoes. The house is great for up to two couples looking to catch up and explore the surrounding area.

Sep 16 – 23

G$37,119 GYD per night

Guest favorite

Cabin in New Oxford

4.9 out of 5 average rating, 605 reviews

Conewago Cabin - Near Gettysburg!

Rustic, cozy one-room apartment down a long lane on the Conewago river. The apartment is attached to the house but has its own entrance without going through the main house. Private bathroom and shower included. PLEASE NOTE: There are several steps in the cabin going down into the kitchen, up into the living room, and down into the bedroom nook. The floor of the bathroom is not completely even. This cabin may not be suitable for senior citizens or those who have problems with mobility.

Mar 10 – 17

G$14,246 GYD per night

Guest favorite

Cabin in Colonial Beach

4.97 out of 5 average rating, 105 reviews

Spring Perfect, Water Front A-frame on Winery

This serene cabin is on the Ingleside Vineyard's property. Have a glass or two of wine and walk around the vineyards and then retreat to your own private a-frame cabin oasis. A beautiful view of the Roxsbury Estate where abundant wildlife can be viewed all around the property and the pond is stocked and ready to be fished. Within driving distance to wineries, Stratford Hall, George Washington & James Monroe's birthplace, Westmoreland State Park, and the beach town of Colonial Beach.

Nov 13 – 20

G$27,882 GYD per night

Guest favorite

Cabin in Cape Charles

4.96 out of 5 average rating, 100 reviews

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Sep 25 – Oct 2

G$45,312 GYD per night

Guest favorite

Cabin in Reedville

4.97 out of 5 average rating, 190 reviews

Dinna Fash-3 BR Waterfront Log Cabin

Welcome to “Dinna Fash,” our cozy waterfront cabin on the Little Wicomico River. Whether you need a change of scenery while working virtually with our high speed internet and fully equipped kitchen, or just some R & R, “Dinna Fash” is it! Bring your kayaks and paddle boards to explore the beautiful waterway that opens up to the Chesapeake Bay. Watch the boats troll by from our natural rock fire pit and comfy Adirondack chairs.

Nov 21 – 28

G$33,485 GYD per night

Guest favorite

Cabin in Shepherdstown

4.95 out of 5 average rating, 423 reviews

The Log Cabin

A restored 1700's log cabin in a convenient location to Shepherdstown and surrounding attractions. One bedroom upstairs with a queen sized bed. One pull out sofa in the downstairs living area. In the summer of 2018, we have added an intimate brick patio area suitable for alfresco dining and for fireside sitting. It is peaceful. It is beautiful. You will not want to leave.

Dec 18 – 25

G$21,981 GYD per night

Guest favorite

Cabin in York Haven

4.95 out of 5 average rating, 498 reviews

Conewago Cabin #3 (No Cleaning Fee!)

All are welcome in our cozy 1 Bedroom plus loft Cabin #3 along the Conewago Creek. Peaceful and relaxing, & the creek is just a step away and is great for splashing around in the summer to cool off. No smoking. Fully equipped kitchen & Washer and Dryer. Carport parking space. Pets are welcome. All pets must be disclosed prior to check in and agree to a $20 pet fee.

Jan 13 – 20

G$25,486 GYD per night