Holiday houses in Newcomb

Apartment in Saint Michaels

4.91 out of 5 average rating, 175 reviews

Charming Studio in the heart of St. Michael's, MD.

Welcome to Lucky Ducks Studio! Enjoy a fully renovated furnished studio in the heart of St. Michael's, MD. Located on Talbot Street in the historic 1850’s McMillian House, the 2nd floor studio offers couples a cozy "British" style experience that sleeps 4 (queen size bed & sofa that transitions to queen), a full bath with a claw tub and a gorgeous industrial style kitchen. Your steps away from the Miles River, shopping, museums, restaurants, breweries and wineries. Free WIFI and YouTube TV.

4.94 out of 5 average rating, 139 reviews

Home in Cambridge

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

4.99 out of 5 average rating, 120 reviews

Guesthouse in Cambridge

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

5 out of 5 average rating, 102 reviews

Home in Saint Michaels

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!

4.99 out of 5 average rating, 603 reviews

Guesthouse in Easton

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

4.89 out of 5 average rating, 599 reviews

Tiny home in Cambridge

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette, making your visit even more memorable! Just a 5 min drive from Blackwater Refuge! It's an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! The Tiny Cabin is located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

Cottage in Saint Michaels

4.97 out of 5 average rating, 164 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

4.86 out of 5 average rating, 141 reviews

The Farm House at Hunting Creek - Pets $50 a night

Description: Beautiful, gated estate carriage house with meadow and panoramic farm views and abundant wildlife. 80 acres- with Water Access at designated pathways Kitchen, Dining Room, and Living Room Sleeps 10 people 5 bedrooms with 7 beds + 2 full baths 5 Full size beds (1 on 1st floor will full bath) 2 Queen size beds Satellite& Wi-Fi Pet Friendly 10 minutes to Easton shops, restaurants and bars 15 minutes to Historic St. Michaels shops, restaurants, and bars

Cottage in Saint Michaels

4.98 out of 5 average rating, 237 reviews

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

5 out of 5 average rating, 106 reviews

Cottage in Easton

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Guest suite in Saint Michaels

4.78 out of 5 average rating, 358 reviews

Gorgeous Cottage: Easy Walk into St Michaels Town!

Gorgeous, sunny former artist loft with great views. Across from Miles River & harbor. Walk to town! Shopping, brewery, winery, museum, restaurants await! Located in historic Bentley Hay, the lodge is perfect for relaxing walks while runners and bikers explore spectacular sights, including the nearby St Michaels Nature Trail. Or rent a kayak and explore San Domingo Creek! NO PETS OR SMOKING. 4 GUESTS MAX BY LAW. Talbot Co License STR-716-KIM

4.96 out of 5 average rating, 113 reviews

Guesthouse in Oxford

The Nichols House Cottage

This lovely guest cottage is located in the historic district of Oxford, walkable to town attractions and restaurants. While the main house is a registered historical property built in the 19th century Victorian style, the guesthouse is charming and well decorated with modern comforts. The cottage is completely independent from the main house. Make this your special place for a romantic getaway at any season of the year.

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Other great holiday rentals in Newcomb

5 out of 5 average rating, 10 reviews

Home in Saint Michaels

Margaret Wells House - New

MarieRating, 5 stars3 days ago

Beautiful historic restoration in an equally beautiful area. House is comfortable, clean quiet, and spacious. Perfect location for a trip to St. Michael’s.

5 out of 5 average rating, 5 reviews

Eastern Shore Family Getaway

JuliaRating, 5 stars1 week ago

Thank you so much Mariana and family! Wonderful stay with an epic half ironman finish to end an amazing weekend! Would 100% recommend for a peaceful weekend!

Home in Cambridge

4.87 out of 5 average rating, 127 reviews

Dorothy's Chesapeake Delight

Amy HRating, 5 stars1 week ago

This location was absolutely stunning. Being on the water, having a fire in the fire pit, watching the sunset…everything was amazing! The shower in the bathroom is super vintage and cute. I had never seen one like it in person. Since we went in late spring there were a lot of mosquitoes so bring bug spray or wear long clothes. The house was very cozy and clean. Check in was a breeze. There are a lot of restaurants and stores within 30 mins of the house. Overall, it was a very memorable stay and I would absolutely book again!

5 out of 5 average rating, 10 reviews

St. Michaels Waterfront Home with Private Dock

StephanieRating, 5 stars1 month ago

The house/setting was even better than pictured. It was really charming and comfortable without being over the top. There was everything we needed, including the kayaks which were a big hit with my family. Great kitchen, really comfortable bedrooms with beautiful water views. The location is perfect, close to both Easton and St. Michaels. We look forward to staying there again when it’s a bit warmer so as to take advantage of the outdoor seating on the spacious lawn. Lisa was beyond responsive and helpful.

5 out of 5 average rating, 4 reviews

Arcadia Shores On The Cove

TiffanyRating, 5 stars6 days ago

Absolutely perfect stay! The house was spotless, beautifully maintained, and exactly as described—if not better. It had everything we needed: comfortable beds, a fully stocked kitchen, fast Wi-Fi, and a peaceful outdoor space to relax. The location was ideal for exploring Easton Maryland—close to charming small towns, the water, and great restaurants. The hosts were incredibly responsive and made check-in a breeze. Highly recommend to anyone looking for a relaxing and comfortable getaway!

Guesthouse in Stevensville

4.99 out of 5 average rating, 278 reviews

Waterfront Getaway - View of bay from your bed

Diane Rating, 5 stars2 weeks ago

This is a perfect location for a relaxing vacation. The views are just stunning and the property is very well cared for. Andy and Rachel are the perfect host, they want you to feel at home. Every detail in the adorable studio apartment has been carefully thought out. And it’s dog friendly! I would highly recommend.

Cabin in Saint Michaels

5 out of 5 average rating, 3 reviews

Serene Waterfront Retreat – Chesapeake Bay Escape

JamesRating, 5 stars6 days ago

Elizabeth's house was perfect for our weekend stay in St. Michael's. The house sits right on the water about a 5 minute drive from the center of town. It was the perfect home base for the Ironman event we were attending in Cambridge. Elizabeth was incredibly responsive and provided thoughtful recommendations for our stay. If we are in the area again we will certainly stay again.