Vacation rentals with a pool in Queen Anne's County

3 bedroom home with pool and game room

Forget your worries in this spacious and serene space. 5 miles outside of the town of Centreville. 15 miles to Chestertown. Custom built home sits on 4 acres in the middle of a 200 acre farm. First floor master bedroom and master bath. Living room, half bath, kitchen and dining area. Large back porch facing pool. Second story has full bathroom and two bedrooms. Each bedroom has an extra room inside. Also upstairs is a game room with a pool table. 1-king bed 1-full bed 1- queen bed 1- twin

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

Heron Roost

Heron Roost is a centrally-located waterfront apartment on a private gated lot with a heated pool. The view from your sun deck is the best on the property with spectacular sunrise and moonrise. We are conveniently located about one mile from the Chesapeake Bay Beach Club and twenty minutes from the US Naval Academy in Annapolis. There are numerous excellent restaurants and bars nearby and the towns of Easton and St Michael’s are close. Please come and enjoy our peaceful and unique property.

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

Waterfront | Swim Spa + Sauna + Beach + Game Room

Escape to Oyster Bay Getaway, a stunning 4-bedroom waterfront retreat designed for relaxation and fun. Enjoy serene water views throughout the home, unwind in the swim spa or sauna, and cozy up by the indoor fireplace. Step outside to a private dock and fire pit perfect for evenings under the stars. The garage game room (unconditioned) and indoor lounge with poker table make this the ideal getaway for families and groups seeking comfort, entertainment, and a true waterfront experience.

Waterfront Wellness - *With Pool and Hot Tub!*

Welcome To Paradise! 🌊 Private Beach | 🏊 Heated Pool | 🔥 Sauna | 💦 Hot Tub| 🌅 Sunset Views This Chesapeake Bay retreat features a private beach, heated pool, sauna, hot tub, and guest house in a peaceful waterfront neighborhood. Enjoy coffee on the deck, afternoons swimming or kayaking, and evenings watching sailboats pass as the sun sets over the bay. Just minutes from historic downtown Chestertown, shops, restaurants, and marinas for the perfect Eastern Shore getaway.

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Optional Heated Pool + Hot tub + Fire Pit+ Fenced

Escape to this luxurious country retreat in Centreville MD, where modern elegance meets tranquil outdoor living. This professionally designed home offers an exceptional blend of comfort & style, perfect for those seeking relaxation & entertainment. The outdoor area is an entertainer's dream, featuring an inground pool, a 12-person fire pit, an 8-person hot tub, & an outdoor kitchen. This luxurious country haven provides all the amenities needed for an unforgettable stay!

Private Pool | Chef's Kitchen | Queenstown

Float the afternoon away in your own private pool, then fire up the grill on the new deck. This single-level Queenstown home sits on a huge, tree-lined lot with a vaulted great room, a two-island chef's kitchen, and a second living room with a brick fireplace. Two bedrooms and three full baths sleep 7 with room to spread out. Queenstown Harbor Golf is 4 miles, the Premium Outlets 4 miles, and Kent Island 12 miles. Free parking with plenty of room for vehicles.

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Bay Bliss House

Welcome to Bay Bliss House - your cozy escape on the Chesapeake Bay, directly facing the iconic Bay Bridge. Enjoy stunning water views and breathtaking sunsets from this peaceful getaway. Perfect for relaxation—not parties—this tranquil home accommodates a maximum of 5 guests at all times. Take a dip in the private pool (May - end of September) and unwind in serenity by the bay.