Holiday houses in Friendship

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Top-rated holiday rentals in Friendship

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Guest favourite

Apartment in North Beach

4.96 out of 5 average rating, 104 reviews

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

22–29 Apr

$249 NZD per night

Guest favourite

Townhouse in North Beach

4.96 out of 5 average rating, 166 reviews

Plant-Filled Oasis near Beach Town w/Passes, Tips

Welcome to A Haven Away! Relax in a plant-filled oasis which offers the perfect setting to unplug, relax, and connect with loved ones. Its prime location is in walking distance to ice cream, coffee shops, lots of fresh seafood, and wetlands. We can't wait to share our local recommendations so you can enjoy our little slice of heaven. 12 min walk to the beach, boardwalk, restaurants, and kids play areas in cute North Beach, MD 7 min drive to Herrington Harbor Find us on IG @ahavenaway

13–20 Oct

$704 NZD per night

Guest favourite

Cottage in North Beach

4.94 out of 5 average rating, 126 reviews

Club Carp North Beach - Steps to the Bay!

Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with three bedrooms and two full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced yard with a swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars. (We are at Dayton and 7th st).

6–13 Sep

$436 NZD per night

Guest favourite

Guesthouse in Galesville

4.95 out of 5 average rating, 164 reviews

Gorgeous water view studio!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

29 Sep – 6 Oct

$355 NZD per night

Guest favourite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

14–21 Dec

$228 NZD per night

Guest favourite

Guest suite in Upper Marlboro

4.95 out of 5 average rating, 104 reviews

Private Apartment on a Horse Farm

My place is convenient to Joint Base Andrews (20 minutes), Washington DC and Annapolis MD (both are about 40 minutes by car) but you’ll love my place because of the outdoor space and the peace and quiet. For Equestrians, we are within 10 minutes of the Prince George's Equestrian Center as well. My place is good for couples, solo adventurers, families (with kids), and well-behaved pets. With a full-sized kitchen, this apartment is a great home away from home.

26 May – 2 Jun

$180 NZD per night

Guest favourite

Home in Deale

4.98 out of 5 average rating, 113 reviews

Chesapeake Waterfront-Hot Tub-Kayaks-King Bed

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Bring your own boat! Make wonderful memories. Great place for families and multi family groups.

23–30 May

$993 NZD per night

Guest favourite

Home in Deale

4.99 out of 5 average rating, 125 reviews

Hannah’s Hideaway

Cottage style with water view of Rockhold Creek. Water taxi right out front of house to take you to local restaurants. Crabbing excursions or fishing charters available for extra cost. Dog friendly. Local restaurants all within 1 mile from location. Fenced in back yard. Picnic table and fire pit to have own personal crab feasts or cookout. Many local restaurants with outside musicians.Grocery store and gas/liquor stores within 5 minutes from house.

26 Apr – 3 May

$466 NZD per night

Guest favourite

Apartment in Huntingtown

4.89 out of 5 average rating, 18 reviews

Private Apartment On An Animal Sanctuary

Private one bedroom apartment with 1 queen bed and a private entrance on a working animal sanctuary including a bathroom, eat in kitchen, work space, living room with 3 sofas & private washer/dryer. Parking has security cameras. Surrounded by trees in Calvert County, your stay will be peaceful. You can interact with the critters or observe from afar. We currently have; geese, ducks, chickens, turkeys, a pig, parrots, emus, cats.....

7–14 Feb

$184 NZD per night

Guest favourite

Home in Tracys Landing

4.99 out of 5 average rating, 166 reviews

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower.

5–12 Dec

$907 NZD per night

Guest favourite

Cottage in North Beach

4.96 out of 5 average rating, 274 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

26 Jul – 2 Aug

$509 NZD per night

Guest favourite

Guesthouse in Annapolis

4.97 out of 5 average rating, 197 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Recently renovated (Feb. 2021) one bedroom Guesthouse with fully equipped kitchen, new king sized bed with premium Saatva mattress, full bathroom and large living room in a quiet neighborhood near the South River, Quiet Waters Park and downtown historic Annapolis. We employ professional cleaning services between each guest stay.

17–24 Nov

$232 NZD per night