Vacation rentals in Point Lookout

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Top-rated vacation rentals in Point Lookout

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

ValueLocationBreakfast

4.97 out of 5 average rating, 472 reviews

Guest favorite

An open layout living area features a kitchen equipped with stainless steel appliances and a breakfast bar with high stools. A dining table is visible in the background near large windows. The space is complemented by two leather couches and light hardwood flooring.

Home in Arnold

Rachel's BnB

A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

FamilyValueCheck-in

4.9 out of 5 average rating, 154 reviews

Guest favorite

An 80-foot private pier extends over calm water, lined with posts and surrounded by greenery. Two personal watercraft and a yellow pedal duck are visible at the end of the dock. The tranquil scene is enhanced by a blue sky with scattered clouds.

Home in Riviera Beach

Waterfront Cheerful 5 home

Welcome to this brand-new relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 4 Bathroom .one bedroom on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

ValueLocationLayout

4.94 out of 5 average rating, 181 reviews

Top guest favorite

A spacious living area, featuring a small sectional couch facing a TV mounted on the wall. A foosball table occupies the foreground, while a dining nook with a round table and chairs is visible in the background. Soft artificial lighting enhances the relaxed setting.

Home in Crownsville

"Hilltop Hideaway"- Private basement suite

Location, location! "Hilltop Hideaway" is a private basement apartment just 16 miles from BWI airport, 10 miles from Fort Meade and Annapolis, and less than 30 miles to Baltimore and Washington, DC! Nestled in a wooded setting on 2 acres, it is perfect for 1-2 adults (25yrs old or older). Not suited for children. Offers living space, bathroom, kitchenette w/microwave, toaster oven, coffee maker, crock pot, apartment size fridge and separate dining nook. Private key code entrance and parking.

FamilyValueQuiet

5.0 out of 5 average rating, 121 reviews

Guest favorite

The entrance of the guest cottage is framed by a charming picket fence, featuring a blue door and a welcoming porch. A small table with two chairs and an umbrella is situated on a wooden deck, surrounded by lush greenery.

Guesthouse in Annapolis

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

LocationValueKitchen

4.9 out of 5 average rating, 367 reviews

Top guest favorite

Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.

FamilyLocationBeach

5.0 out of 5 average rating, 217 reviews

Guest favorite

Guest suite in Annapolis

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

FamilyLocationKitchen

4.94 out of 5 average rating, 147 reviews

Top guest favorite

Home in Odenton

Train Tracks Getaway (Whole house)

All aboard for comfort and charm at Train Track Getaway! This cozy Odenton home is perfect for families and friends, with easy MARC train access to D.C. and Baltimore. Enjoy pancakes on the back porch and marshmallows by the firepit—yes, we’ve got the s’mores kit ready! Inside offers comfy beds, a full kitchen, and space to relax or play. Whether you're visiting Fort Meade or just unwinding, this is your laid-back home base for fun, family, and firepit vibes.

FamilyValueBackyard

4.96 out of 5 average rating, 114 reviews

Top guest favorite

Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

Enjoy a peaceful waterfront getaway just 2 miles from Historic Downtown Annapolis and the U.S. Naval Academy. Located directly on the South River in a quiet neighborhood, this charming cottage features a full kitchen, 1 bedroom, washer/dryer, and sleeper sofa for up to 4 guests. Relax on the private patio with outdoor seating, grill, and fire pit, or enjoy the beautiful river views. Perfect for exploring Annapolis or simply unwinding by the water.

FamilyValueView

5.0 out of 5 average rating, 226 reviews

Top guest favorite

A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.

Place to stay in Glen Burnie

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

LocationValueCheckout

4.94 out of 5 average rating, 413 reviews

Top guest favorite

A spiral staircase leads to a lofted sleeping area in a well-lit living space. Warm wood tones are present in the furniture and flooring. A small kitchen area is visible, along with a dining table set for four. Lighting fixtures enhance the modern feel.

Guesthouse in Annapolis

Garden View, 1 Bedroom and a Loft.

Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.

LocationValuePets

4.99 out of 5 average rating, 167 reviews

Top guest favorite

Cottage in Annapolis

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

LocationValueAccess

4.98 out of 5 average rating, 167 reviews