Newcomb Holiday Rentals

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Holiday Rentals in Newcomb

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland

Walk to Everything House

10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (4)
"We had the most wonderful time at this charming house on Tillman Island! While the pics are great, it is even better in person. The house is perfectly nestled on the waterway, offering stunning views. The backyard pool was a true highlight, and we spent countless hours splashing around, the pool in the sun."
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (134)
"We loved this house, it was perfect for exploring town and as a base for things further afield. Comfortable, thoughtfully and well stocked with lots of charm."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (17)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (30)
"Excellent experience."
The price is AU$404
includes taxes & fees
2 Dec - 3 Dec
Relax on Kent Island in 3 Bedroom Home w/Waterview

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (32)
"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (87)
"All as advertised Wonderful option to a hotel"
Cass-Away Luxury Houseboat

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (168)
"We went to St. Michael’s for a wedding. The cottage was great. Very charming. The location was perfect. We could walk everywhere. We had great communication with the host. He was very accommodating. We will stay there again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Pool and Bay Views on wrap around deck in Kent Island

9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (17)
"Very relaxing"
Cass-N-Reel Luxury Houseboat

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (32)
"Perfect large space on a quiet and pretty area. Really great space. "
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10.0 out of 10, Exceptional, (7)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (37)
"Every morning I made coffee, lit the fire pit on the dock and spent at least from 30 minutes before sunrise to 30 after. Used Merlin to identify bird calls. Heard and saw bald eagles, a belted kingfisher and an eastern bluebird. Watched a great blue heron fishing. Heard many many different birds. Truly an awesome location to slow down and enjoy the moment "
The price is AU$436
includes taxes & fees
15 Dec - 16 Dec
Waterfront Getaway with Dock

Cottage on Cabin Creek

10.0 out of 10, Exceptional, (100)
"I highly recommend staying here for a cozy couples weekend. It was absolutely beautiful and quiet. The host was so nice and made us feel welcome. I can’t wait to stay here again."
The price is AU$566
includes taxes & fees
11 Dec - 12 Dec
Cottage on Cabin Creek

New! Stylish downtown home w/awesome outdoor area!

10.0 out of 10, Exceptional, (21)
"Great stay, clean and spacious. Lovely outdoor seating area. Convenient to the town of Stevensville, shopping and dining options, coffee house and great location for Kent Island and Annapolis. Loved the home and would definitely stay again! "
New! Stylish downtown home w/awesome outdoor area!

Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

9.8 out of 10, Exceptional, (6)
"We enjoyed our time at the house very much. We went out to dinner only once and the rest of the time we ate in. We grilled two nights and made a roast one night. The views and the pool were more than you could imagine."
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

10.0 out of 10, Exceptional, (118)
"comfortable and very cozy. Wonderful crabbing and sunsets."
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!

9.8 out of 10, Exceptional, (9)
"Our stay was amazing. The house is beautiful. The views and peaceful location were completely used. We had many fun game nights and dinners around the table, the kitchen easily provided many happy meals. The gas grill, the fire pit were easy to use. The kayaks were a lot of fun. Sitting on the dock enjoying the peaceful quiet mornings was rejuvenating. The pool chairs and umbrellas were really nice. A ping pong table in the garage was a ton of fun too. The extra fridge/freezer was handy and the...
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Newcomb you may be interested in

Hyatt Regency Chesapeake Bay

4.0 star property
8.8 out of 10, Excellent, (1064)
"Anniversary. Great time. Beautiful property "
The price is AU$370
includes taxes & fees
2 Dec - 3 Dec
Hyatt Regency Chesapeake Bay

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (441)
"Beautiful venue. Exceptionally clean. Great service. Walking distance to two good restaurants. Had a room with two queen beds. Beds are a little too soft for our liking. Other than that, it was a perfect stay. "
The price is AU$232
includes taxes & fees
2 Dec - 3 Dec
Hyatt Place Kent Narrows & Marina

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (322)
"Everything about this property was exceptional! Definitely will be back!"
The price is AU$535
includes taxes & fees
17 Dec - 18 Dec
Inn at Perry Cabin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Newcomb?

Yes, there are holiday rentals close to the most popular sights in Newcomb, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Newcomb has to offer?

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!: This holiday home rental outside of Newcomb is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

What can I see and do in Newcomb?

Explore the area and family-friendly sights such as Chesapeake Bay Maritime Museum, or get out into nature at a spot like Great Marsh Park. St. Michaels Winery and Avalon Theatre are a couple of places you'll find in the wider area.

What are holiday rentals like in Newcomb?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Newcomb. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.