Holiday rentals in Silver Spring

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Top-rated holiday rentals in Silver Spring

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Top guest favourite

Guest house in Annapolis

5 out of 5 average rating, 156 reviews

Private Art-Filled Guesthouse near Naval Academy

Slip under a colorful quilt and get a great night's sleep in a secluded walk-up guesthouse. An intriguing blend of antique curios and Americana populates the room. The result is a comforting space that also has a modern kitchen and updated bathroom. Homeowners on site and available to book your Treetop Getaway! Key code access will be provided. Check in time is 3pm. Check out time is 11am. Contact me via phone or through messages here and I will respond as soon as possible. The guesthouse is in West Annapolis, a residential neighborhood bounded by Weems Creek and the Severn River. It's close to downtown, the Naval Academy, and the Stadium. Quaint shops and restaurants are just around the corner.

Guest favourite

Cottage in Edgewater

4.99 out of 5 average rating, 155 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Guest favourite

Cottage in Leesburg

4.92 out of 5 average rating, 408 reviews

Romantic Stone Cottage Circa 1869-75 acres to Hike

Plan a getaway in our newly renovated Stone Cottage nestled on hilltop just 15 minutes from Leesburg & less than 90 minutes from DC. The property adjoins next to a hidden state park, not on the map with gentle hiking trails. Secluded location however 10 min to some of the areas finest wineries & breweries. Custom-made king-size bed and fresh interior, are sure to impress . So whether you are visiting for a wedding, exploring wine country or in need of a quiet setting, we invite you to enjoy!

Superhost

Home in Shady Side

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

Accepting 2025 bookings as of June 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.

Top guest favourite

Cottage in North Beach

4.98 out of 5 average rating, 151 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

Guest favourite

Flat in Annapolis

4.92 out of 5 average rating, 101 reviews

Dazzling day/night water views,1st class amemities

TREAT YOURSELF! YOU DESERVE THE VERY BEST! HUGE DISCOUNTS FOR WEEK AND MONTH LONG STAYS! Treat yourself to the good life while in Annapolis! Gorgeous 14yr. old custom designed & furnished 1470sq.ft. waterfront apartment, 9ft. ceilings, fantastic water views day & night! Private pier, firepit and 40ft. waterfront covered patio for guests use. Guest parking for 4 cars. Few minutes to US Naval Academy, Annapolis Harbor, restaurants, shopping. Pet-friendly, must be cleared with host. *see below*

Guest favourite

Home in Deale

4.88 out of 5 average rating, 100 reviews

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.

Guest favourite

Cottage in Pasadena

4.88 out of 5 average rating, 124 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Top guest favourite

Guest suite in Leesburg

4.94 out of 5 average rating, 124 reviews

Stunning Views in Spacious Unit

Welcome to our gorgeous apartment in Virginia's wine country! Enjoy a private entrance, kitchenette, and a beautiful master bedroom. Our location puts you just 5 mins away from restaurants, breweries, hiking trails, and downtown Leesburg. Use our 2 available bikes to explore. Stay connected with fast Wi-Fi and unwind on the patio with expansive views. Free parking and nearby Walmart make stocking up easy. Let us make your stay in Leesburg unforgettable!

Guest favourite

Home in Arlington

4.84 out of 5 average rating, 113 reviews

Next to Virginia Hospital Center

Welcome to your future home away from home! This stunning 5-bedroom single-family corner house is the epitome of comfort and convenience. -A step a way from VHC hospital. - Metro bus stop at the end of the block - 5 car parking lot - has access to house without stairs, and walk in shower for those experiencing difficulty with movement or stepping over tub. -sleeps 10 guests comfortably (3 queen beds, 4 twin beds) -1.4 miles from Ballston metro stop

Guest favourite

Guest house in Frederick

4.98 out of 5 average rating, 181 reviews

Romantic Getaway - Heated Spa Open Year Round

Enjoy our beautifully decorated four bedroom home, furnished with unparalleled elegance and style. This tranquil guest house is located less than an hour from Washington DC and Baltimore, MD, and a half-hour from Gettysburg and Harper's Ferry and offers luxurious rooms with unparalleled elegance and style. For the ultimate pampered experienced, guests can arrange for in-house spa services such as a full-body therapeutic massage.

Guest favourite

Apartment in Bethesda

4.9 out of 5 average rating, 191 reviews

Bright 2br w amazing loc and view

850 sq ft 2 bedroom 1 bathroom condo in great downtown Bethesda location. Corner unit with windows everywhere making for great light, energy, and views. Balcony overlooking one of the main Bethesda squares. Close to metro and walkable to more restaurants and bars than you can possibly try. Tandem parking for two cars. New flooring as of June 2023. This condo will exceed your expectations.