Holiday rentals in Arnold

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.

4.96 out of 5 average rating, 669 reviews

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!

4.94 out of 5 average rating, 174 reviews

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.

4.98 out of 5 average rating, 103 reviews

Home in Annapolis

Hot Tub Haven: Annapolis Backyard Oasis

A serene escape awaits you at our cozy 4-bedroom retreat, just minutes away from Historic Downtown Annapolis. As the sun sets, the deck comes alive under the soft glow of string lights beckoning you to unwind in our 8-person Bullfrog hot tub or outdoor firepit where your worries will melt away! Indulge in the culinary delights of fresh local seafood and world-renowned crabcakes just moments away. Truly indulge in our paradise getaway and experience everything Historic Annapolis has to offer!

5 out of 5 average rating, 10 reviews

Waterfront Home, Amazing Views near Annapolis

Invite friends and family to experience a serene retreat on the Magothy River, close to Annapolis. This stylish yet cozy waterfront residence offers stunning views and many outdoor activities. Watch boats and wildlife from the private pier, screened porch and fire pit area. Putting green, bocce, grill & smoker available! Recently renovated kitchen ensures effortless gatherings. The upper-level loft, furnished with comfortable sectional & air mattresses, enhances the versatility of your stay.

4.9 out of 5 average rating, 288 reviews

Guest house 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.

4.87 out of 5 average rating, 135 reviews

Cozy Comfort - only 7.5 Miles to Annapolis & USNA

Private first-floor guest apartment, a quiet retreat in a lovely residential neighborhood close to downtown Annapolis. It has 2-bedrooms, a living room, mini sit-in kitchen, bathroom, and laundry room. It’s ideal for travelers who want privacy, and a little more space than the usual stay. Sip your morning coffee in the gazebo and unwind after day trips fireside on the comfy sectional. The kitchen is ideal for enjoying light cooking or take outs. Comfy queen sized beds with crisp linens.

4.93 out of 5 average rating, 41 reviews

Cozy Arnold House Near Annapolis

Larger groups should consider our Deluxe Upgrade: https://www.airbnb.com/h/arnoldhouseandstudio Your family will be close to everything Annapolis has to offer when you stay at our cozy Arnold home. This home is located across the Naval Academy Bridge and just 10 min from Downtown Annapolis, United States Naval Academy & Naval-Marine Corps Memorial Stadium. This home sits on a quiet road on a private wooded lot with plenty of space for entertaining friends and family during your stay.

4.9 out of 5 average rating, 203 reviews

Home in Annapolis

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

5 out of 5 average rating, 235 reviews

Guest suite in Annapolis

Cape St Claire waterfront getaway "The Apartment"

This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.

4.94 out of 5 average rating, 175 reviews

Flat in Arnold

Celebrate Summer by Your Private Pool

Lovely 2 acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

4.97 out of 5 average rating, 39 reviews

Mins to Annap; Luxury Townhome

Visiting the Annapolis area? Stay in style in this very spacious 3-bed, 3.5-bath 3-level townhouse. Sleeps 8 very comfortably in 1 king bed, 2 queen beds, and 2 twin floor mattresses. Two super comfy hang-out areas inside, 2 outdoor living areas, a fully-stocked gigantic kitchen, a large dining room. Comes stocked with all bedding and towels, as well as common guest supplies. Just 14 minutes to downtown Annapolis. Restaurants and shopping are all around. Book your stay today!

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Other great holiday rentals in Arnold

4.85 out of 5 average rating, 548 reviews

Sunny Spot Suite, Serene, Annapolis, Naval Academy

LindsayRating, 5 stars6 months ago

Sharon’s place was just as described. It was a convenient home base close to our family that we were visiting. We were very happy that our dogs were able to join us. There are a decent amount of steps down to the suite that we had to assist our senior pups with. The suite was clean and had a basic kitchen set up good for coffee in the morning or reheating take out. The location was very convenient to all local things to do. We were very happy with our stay.

5 out of 5 average rating, 7 reviews

Cozy & Modern Upper Level Suite

LoriRating, 5 stars1 month ago

I’ve stayed in a lot of Airbnb properties and Whytnie’s is one of the cleanest and best maintained I have ever seen. The bed was comfortable as was the furniture and the kitchen was well equipped. I sat out on the deck one evening which was pleasant and there is a large backyard that kids could run around in. Whytnie responded quickly to a kitchen question I had and that was super helpful. We would definitely stay there again as the location worked well for our needs.

5 out of 5 average rating, 37 reviews

Cottage in Arnold

Rare Find 5 Star, No Cleaning fee, Salt Water Pool

CeciliaRating, 5 stars9 months ago

Katie’s place was a wonderful place for a weekend reunion with friends. The house was clean, comfortable and pretty - exactly as advertised and as shown in the pictures. The beds were comfortable and the kitchen well-stocked. The outdoor garden and pool were lovely and had lots of comfortable seating areas. The house was an easy drive to Annapolis for restaurants and shopping but had a great movie watching set up that would be great for a rainy day. Nearby nice grocery store.

4.98 out of 5 average rating, 115 reviews

Cottage in Annapolis

Weems Creek Cottage, Annapolis Waterfront

AmyRating, 5 stars1 day ago

Cottage is very cute and the perfect size for a couple. Beautiful view and has all the necessary amenities. Jim was very responsive and communicative!

Cottage in Arnold

4.73 out of 5 average rating, 52 reviews

Sail, Power Boat into Deep Creek Arnold Getaway

GeorgeRating, 5 stars6 days ago

We had a great stay! The owner was incredibly friendly and responsive, which made everything easy. The deck was a highlight—spacious with a beautiful, scenic view of the water. We especially enjoyed having access to the free kayaks and the private dock—it was such a peaceful and relaxing spot. The location was also convenient, with a great local restaurant just a short walk away. Would definitely recommend this place for a relaxing getaway!

4.93 out of 5 average rating, 14 reviews

Home in Crownsville

Welcome to Heron House! Annapolis Waterfront Oasis

JenniferRating, 5 stars1 week ago

Very peaceful surroundings, you are out on a point overlooking the bay, with lots of outside space to relax in the mornings to enjoy your morning tea/coffee. I loved having the real fireplace and enjoyed an evening fire on the more chillier evenings. Felt at home and comfy.

4.93 out of 5 average rating, 42 reviews

Guest suite in Annapolis

Bayside Beach Getaway

MollyRating, 5 stars1 month ago

We were absolutely delighted with our stay! Squeaky clean, super comfortable bed, well appointed kitchen and it felt like we were in a tree house. We loved walking and sitting on the private beach and the location was so private, peaceful and relaxing. Would highly recommend! Thank you, Allison, for a lovely stay.