House holiday rentals in Glassmanor

Modern luxury waterfront retreat, 1 hr to DC

Expansive river views from every room and on your bed! A luxurious waterfront retreat. Relax in a full marble tiled, oversized rainfall shower, rich cotton sheets and pillowtop bed. Full kitchen with Nespresso and tea. Cul-de-sac house, on a cliff with private deck/dock. High ceilings and massive windows let in lots of light. Easy access to dining, wineries, farms, beaches, and historic sites. DC/VA easy 1 hr drive away. *Host lives in adjoining building, attached guest house is fully private.

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Waterfront, Dog-friendly, Hot Tub, Peleton, Bikes

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

Cattail Landing- Photographer's Waterfront Retreat

Accepting 2025 bookings as of May 1st.... "Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take our kayaks to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acres in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home.

South River Beach Front House

New 2024 Renovated Stunning WATERFRONT South River Beach home!! BEST WATERFRONT LOCATION!!! with heated POOL on the river side & deck 10' from waters edge. Beach, 125' private pier for crabbing & fishing. Comm w/ beach, pier, tennis & basketball courts. (1) Main LVL: entry foyer, sunroom, stunning kitchen, dinning area, & living room w/FP. Main level owners suite w/full bath, & 1/2 bath. (2) Upper level: 2 bedrooms w/ full bath & upper LVL sitting area & sun deck w/expansive river views

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Fabulous 4-5 bedroom 3-bath house with spectacular views on a lush, waterfront point! Shady waterfront lawns & sunny pier, breezy open spaces, sparkling views, & wildlife. Hidden but close to services. Couples & groups love our wonderful, nature-filled spot, a fun, relaxing, serene retreat on the WEST shore of the Chesapeake (close proximity to D.C., Annapolis, Baltimore)! Crabbing, kayaks, fire pit on two country-like acres. See “NEW Amazing” for whole 6-7 bed 4 ba listing of same house.

Eastport Haven House

Welcome to our custom Craftsman in the exclusive Maritime Eastport section of Annapolis. Surrounded by the city's best restaurants ( Ruth's Chris, ChartHouse , Vin 909 and many many others )and home to some very famous neighbors it's one one of the most desirable locations in town. A short stroll across a quaint drawbridge and your downtown for shopping USNA . Very spacious home with 4 bedrooms 4 baths , parking for 4 cars and a pool table. Truly a million plus dollar property !

Cozy Beach House ~Chesapeake Bay Getaway

Beach Access~ a short walk or drive to the community private beach, boat ramp & Flag Harbor Marina. This vintage and cozy style house is well stocked with everything you need for a beach getaway. Enjoy two kayaks, deck with two grills, backyard fire pit and outdoor yard games while relaxing after a fun day at the beach. Come to Southern Maryland and discover fossils, cliffs and the Chesapeake Bay. Budget friendly getaway!

West Annapolis SuperHost!

Welcome! We are eager to continue providing our quests with an upgraded experience. This is a one story house! Best of AirBnb! Perfect location close to art and culture, the city center, and parks. Great house for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). One block from Navy Marine Corps Stadium!