9 Best Hotels in The Eastern Shore, Maryland

Background Illustration for Hotels

Outside of Cambridge's singular Hyatt Regency and Ocean City's approximately 10,000 hotel rooms—the great majority of accommodations throughout this region are B&Bs, inns, and budget chain hotels. The scope of choice is broad, yet as might be expected, the quality and level of service of these smaller enterprises varies dramatically. Many B&Bs and inns have teamed up with other tourism enterprises to create packages that include boating, golf, and tennis, visits to art galleries and museums, and more.

Of note: B&Bs and inns throughout Maryland's and Virginia's Eastern Shore commonly require two-night minimum stays on weekends during periods of high demand, most often throughout the summer months, sometimes in late spring and early fall, and during special events such as town-wide festivals.

Bartlett Pear Inn

$$ | 28 S. Harrison St., Easton, MD, 21601, USA

Natives Jordan and Alice Lloyd returned to their hometown and bought a 220-year-old home (the former Inn at Easton) right in the center of town. They restored the inn, creating seven guest rooms and suites, each named after a different variety of pear. Impeccable hosts, the Lloyds considered every detail, from the luxurious sheets to the brightly colored walls.

Pros

  • Central location
  • Beautiful garden
  • On-site Bartlett Pear Restaurant

Cons

  • Lacks some of the amenities of a large hotel, such as a swimming pool
  • Pets are allowed with a $50 deposit
28 S. Harrison St., Easton, MD, 21601, USA
410-770–3300
Hotel Details
Credit cards accepted
7 rooms
Free Breakfast

Quick Facts

  • $$

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Elk Forge B&B Inn and Retreat

$$ | 807 Elk Mills Rd., Elk Mills, MD, 21920-2207, USA

A 20-minute drive from North East, Elk Forge is nestled among 5 acres of woods and gardens along Big Elk Creek. Each of the 12 guest units is beautifully furnished and uniquely decorated, inspired by area locales and cultures, and creature comforts are plentiful. A daily afternoon tea includes the innkeepers' own herbal blends; services at the Spa in the Garden include Swedish massage and aromatherapy facials. With easy access to sites of interest in Delaware and Pennsylvania as well as Maryland, Elk Forge is indeed a mini-resort.

Pros

  • Attractively priced considering available spa amenities

Cons

  • Might seem somewhat remote to some
807 Elk Mills Rd., Elk Mills, MD, 21920-2207, USA
410-392–9007
Hotel Details
Credit cards accepted
7 rooms, 5 suites
Free Breakfast

Quick Facts

  • $$

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Five Gables Inn & Spa

$$ | 209 N. Talbot St., St. Michaels, MD, 21663, USA

Three circa-1860 houses have been turned into an elegant and comfortable getaway. All rooms have a private porch or balcony, and all are decorated with antique furnishings, fine linens and towels, and down comforters. The hot stone massage and invigorating rosemary mint body wrap are treatments in the spa. Refreshments are served daily at 3. The bed-and-breakfast home also emcompasses a fine needlepoint shop, B's Stitches, and an upscale pet boutique, Flying Fred's.

Pros

  • Allows for easy walking throughout St. Michaels thanks to its main-street location
  • On-site shopping and spa options
  • Fireplace in the room

Cons

  • True resort feel challenged by main-street location
209 N. Talbot St., St. Michaels, MD, 21663, USA
410-745--0100
Hotel Details
Credit cards accepted
20 rooms
Free Breakfast

Quick Facts

  • $$

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Recommended Fodor's Video

Lodgecliffe on the Choptank

$$ | 103 Choptank Terr., Cambridge, MD, 21613-1115, USA

Located on a rise overlooking the river, this elegant turn-of-the-20th-century country home was the first bed-and-breakfast in the county (1986) and remains one of the most charming. Accommodations include the delightfully contemporary second-floor room called Sarah's Loft, named for the original innkeeper. Don't sleep through breakfast or you might miss cranberry French Toast made with sourdough bread, Chesapeake puff pancakes, or phyllo dough egg blossoms, freshly made and hot from the oven and often served out on the screened-in porch. Guests feel like personal guests of the innkeepers and their two young sons.

Pros

  • Traditional B&amp
  • B in the truest sense
  • Less expensive option

Cons

  • Almost too personalized an enterprise for some
103 Choptank Terr., Cambridge, MD, 21613-1115, USA
866-273–3830
Hotel Details
Credit cards accepted
4 rooms

Quick Facts

  • $$

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River House Inn

$$ | 201 E. Market St., Snow Hill, MD, 21863-2000, USA

With its welcoming front porch, this Victorian home and its adjacent cottages are on two lovely acres on the banks of the Pocomoke River. This small inn, on the National Register, is impeccably appointed and maintained, including the lovely gardens. Decor is traditional Early American.

Pros

  • Relaxing riverside setting
  • Attractive for paddlers
  • Complimentary breakfast

Cons

  • May be too quiet for some
201 E. Market St., Snow Hill, MD, 21863-2000, USA
410-632–2722
Hotel Details
Credit cards accepted
Closed Dec.–Feb.
3 private cottages, 4 rooms

Quick Facts

  • $$

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Robert Morris Inn

$$ | 314 N. Morris St., Oxford, MD, 21654, USA

In the early 1700s this building on the banks of the Tred Avon River was crafted as a home by ships' carpenters using ship nails, hand-hewn beams, and pegged paneling. In 1738 it was bought by an English trading company as a house for its Oxford representative, Robert Morris. Four guest rooms have handmade wall paneling and fireplaces built of English bricks used as boat ballast. Other buildings in the complex include a newer manor house on a private beach. Breakfast is included. Several years ago the inn closed its famous restaurant (with its reputed "best crabcakes on the bay"), but in 2010 it reopened, redecorated, and rehabilitated, under celebrity chef Mark Seller, who promotes locally sourced food. The kitchen has regained its former glory.

Pros

  • Whiffs of history exude from every corner
  • Riverfront setting

Cons

  • Three-centuries-old accommodations are difficult to maintain
314 N. Morris St., Oxford, MD, 21654, USA
410-226--5111
Hotel Details
Credit cards accepted
16 rooms
Free Breakfast

Quick Facts

  • $$

Something incorrect in this review?

Ship Watch Inn

$$ | 401 1st St., Chesapeake City, MD, 21915-1227, USA

Three levels of broad decks mean that every room has a place from which to relax and watch all manner of watercraft, including international shipping vessels, sail in and out of the Chesapeake & Delaware Canal just yards away. (A canal-side hot tub offers an even closer view.) Built as a residence in 1920, this elegant, waterfront B&B blends eclectic furnishings with modern amenities. The decades-old black-and-white photos hanging in the public areas reveal much about the roles the owner-innkeepers' families played in the history of Chesapeake City. The Ship Watch is one of several B&Bs in Chesapeake City.

Pros

  • Extraordinary location literally on the edge of the C&D Canal
  • All rooms have a balcony overlooking the water
  • No minimum stay requirement

Cons

  • Few amenities and limited parking
  • In the off-season, a breakfast voucher at a nearby cafe is provided on weekdays
  • No kids under 12
401 1st St., Chesapeake City, MD, 21915-1227, USA
410-885–5300
Hotel Details
8 rooms, 2 suites
Free Breakfast

Quick Facts

  • $$

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Tilghman Island Inn

$$ | Tilghman Island, MD, 21671, USA

Warm and welcoming conviviality and casual elegance define this compact, modern resort overlooking the Chesapeake Bay and a waterfowl marsh. Decor and furnishings throughout are bright and modern, with lots of white enhanced by splashes of color. Five deluxe waterside suites have hot tubs, fireplaces, and spacious decks. The 5-acre complex includes a 20-slip transient marina and a small fleet of tandem and single kayaks available for rent. Dishes served at the Gallery Restaurant ($$–$$$) are at once innovative and traditional, enhanced by a well-selected wine list.

Pros

  • Truly panoramic Bay views
  • Aura of a mini-resort

Cons

  • Not historic setting
  • Lacks the small B&amp
  • B feel of the island's other options
Tilghman Island, MD, 21671, USA
410-886–2141
Hotel Details
Credit cards accepted
15 rooms, 5 suites
Free Breakfast

Quick Facts

  • $$

Something incorrect in this review?

Victoriana Inn

$$ | 205 Cherry St., St. Michaels, MD, 21663, USA

Adirondack chairs line a sloping expanse of lawn leading to the formal gardens of what was once a Civil War army officer's home. Set on the town's harbor and across a footbridge from the Maritime Museum, this inn is a relaxing haven. All rooms include queen-size beds; two have fireplaces, and three overlook the water. The suite has a private water-view deck and a fireplace as well as a TV. There's a nightly happy hour that includes wine, beer, and light hors d'oeuvres. No children under 13 are allowed on weekends.

Pros

  • A revered St. Michaels institution among many favored town sites
  • Most rooms have a fireplace

Cons

  • Minimum of a two-night stay
  • Location near the harbor can be heavily trafficked
205 Cherry St., St. Michaels, MD, 21663, USA
410-745--3368
Hotel Details
Credit cards accepted
7 rooms
Free Breakfast

Quick Facts

  • $$

Something incorrect in this review?