Vacation rentals in Matapeake

4.96 out of 5 average rating, 408 reviews

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.

4.93 out of 5 average rating, 276 reviews

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 15 miles Baltimore- 40 Wash. DC- 45 Easton- 30 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions, including Chesapeake Beaches. This is a Non-Smoking House. Also No Pets Parties & 14 max guests. Book Today!

Apartment in Stevensville

4.98 out of 5 average rating, 278 reviews

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.

4.96 out of 5 average rating, 669 reviews

Guest suite in Arnold

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

4.95 out of 5 average rating, 271 reviews

Home in Grasonville

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

4.94 out of 5 average rating, 176 reviews

Guest suite in Arnold

Coastal Comfort Suite Near Annapolis, Hottub, EV

Hot tub is open for the season. Pool will be open May 12 through Labor Day weekend. Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

Houseboat in Kent Narrows

4.97 out of 5 average rating, 150 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

5 out of 5 average rating, 114 reviews

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

4.9 out of 5 average rating, 288 reviews

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.

Guesthouse in Stevensville

4.99 out of 5 average rating, 278 reviews

Waterfront Getaway - 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.

Guesthouse in Glen Burnie

4.93 out of 5 average rating, 343 reviews

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

4.97 out of 5 average rating, 266 reviews

Apartment in Chester

Cozy Waterfront Apartment Chester, MD

Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy our clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. Plus an easy to assemble blow up air mattress to sleep an additional two. WiFi included. Private porch to enjoy water view!

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Other great vacation rentals in Matapeake

4.97 out of 5 average rating, 74 reviews

Home in Annapolis

Annapolis USNA Cottage Waterfront Pier Cozy Escape

Nate And KatieRating, 5 stars2 weeks ago

Very quiet location but not far from amenities. The home had an attention to detail that not all air bnbs do (for example enough towel hooks for everyone staying!) as well as basic cooking amenities

4.98 out of 5 average rating, 63 reviews

Barn in Queenstown

Waterfront Modern Guest Barn

ElaineRating, 5 stars1 month ago

Overall, I enjoyed the place. The barn was minimalistic and nice for photos. The best part was the waterfront view. The house was very clean and pretty kid friendly (a few high chairs included). The kitchen had the bare minimum to cook and grill with but I wouldn’t say it was fully stocked. I would say in general that we enjoyed our stay. The kayaks were wonderful.

5 out of 5 average rating, 13 reviews

Home in Chester

Spacious waterfront home private pier dog-friendly

DanRating, 5 stars1 month ago

The property, location, house set-up, and communications from the management during our 6 day stay was amazing. Literally the best low-key, relaxing experience I have ever had in recent memory. The house has everything you need for a great peaceful stay, especially if you are just hanging with a small group of close friends. Cooking is particularly awesome, as this property has a great wide open kitchen. The grounds are beautiful. We spent most of our time on the main floor in the kitchen and then on the long beautiful dock where we did some fishing and first time crabbing just for fun. The town nearby and neighborhood is so nice. Not far from Annapolis, MD at all if you want to visit. But honestly, the property alone is so nice to just to stay in and just relax. Great space with some homey accommodations. Big shout outs to one of the property management team members, Melissa. She was so very helpful. Will be back again next year!

5 out of 5 average rating, 22 reviews

Houseboat in Baltimore

Flohom 5 | Stunning Inner Harbor 360° Views

RasheidaRating, 5 stars1 week ago

Nice staycation idea that we used to celebrate our birthdays. Took a water taxi to dinner at Maximom (Four Seasons) and returned to the FLOHOM for drinks on the roof deck with the fire place burning. Quaint stay!

4.98 out of 5 average rating, 42 reviews

Home in Arnold

Rachel's BnB

WendyRating, 5 stars1 week ago

Above & beyond! The home was in a great spot with an excellent price. Tim was extremely accommodating with our requests and communication was perfect. The refrigerator was stocked with eggs and butter. The cupboards were stocked with staples and all the supplies we needed - toilet soap, shampoo, Kleenex, paper towels, bath towels, snacks, granola bars, etc. We would highly recommend this Airbnb to anyone and would use again. Thank you!

Guesthouse in Grasonville

4.9 out of 5 average rating, 229 reviews

Eastern Shore Charm on Winchester Creek

FuadRating, 5 stars1 week ago

Judy's guest house was conveniently close to a weekend wedding getaway for us. she was a attentive and responsive host. checking in on us before, during and after our stay (thank you for letting us know about the purse we left!) her yard let's out to the water front and it's a short drive to anywhere you want on Kent Island. We appreciated her flexibility with checkin/out and the wonderful snacks and fresh muffins.

5 out of 5 average rating, 4 reviews

Bay Bliss House

EthanRating, 5 stars1 week ago

The Bay Bliss House is a wonderful stay! We were in town for a wedding at the Chesapeake Bay Inn and this was the perfect location for us. It is less than 10 minutes away from plenty of restaurants and stores and the neighborhood is lovely/safe. Olga was an extremely kind and responsive host throughout. Her messages in advance of and during the stay were very clear and her replies were timely when needed. She left local recommendations and plenty of amenities within the house for our use. Finally, the house itself is fantastic. Although it was a little cold with the wind off the bay, we thoroughly enjoyed the back patio with the built in pool. The views from relaxing in the sunroom were our favorite part of the trip. I would highly recommend this house for any future travelers.