How much does it cost to stay in house rentals in Olney?

Experience the best of Olney with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Are there vacation rentals with a dedicated workspace in Olney?

Yes! Work meets play with ease at over 10 vacation rentals in Olney featuring dedicated workspaces. Stay connected and productive in your home away from home.

Do house rentals in Olney have air conditioning?

Absolutely! We offer over 10 house rentals with air conditioning in Olney. Enjoy a tailored experience with all the comforts you desire.

What are the most popular amenities for House Rentals in Olney?

Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Olney

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Olney

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A modern kitchen featuring sleek black and white cabinetry, stainless steel appliances, and a minimalist design. The space includes a gas stove, a microwave, and a refrigerator. Natural light comes in through a window, illuminating the wood-like flooring and nearby staircase.

Home in Timonium

4.92 out of 5 average rating, 192 reviews

* Lovely Gem w/ Perfect Combo of Flair & Class *

This is our 5th Airbnb in the Towson / Lutherville area. We know how important it is to feel comfortable & relaxed when you arrive back from a long day of work, sightseeing, visiting with family members, playing sports, etc. This inspiration is seen throughout this entire house and you'll find the house to be a place to recharge, relax and enjoy high end amenities to include HDTVs in living and bed rooms, fully stocked kitchen, plush bedding, luxury shower fixtures, and more. You have to see it!

Guest favorite

Cottage in Middletown

4.9 out of 5 average rating, 275 reviews

Charming "Cream of the Crop" Cape ~❤️of Middletown

Cozy cape in the ❤️ of Middletown, MD. Walking distance (1/2 mile)to quaint Middletown restaurants, shops, & parks. Set your sights on adventure within a short drive. Enjoy downtown Frederick restaurants, shops, parks, & nightlife.Visit the local wineries, breweries & festivals. Hike the Appalachian trail. Float the Potomac River. Bike the C&O Canal. Ski the slopes @ area ski resorts. Golf 18 holes @ the championship golf course. Visit wedding venues. Go antiquing. Tour quaint nearby towns. Etc

Guest favorite

A spacious outdoor area features a large in-ground pool surrounded by a patio. Lounge chairs in a bright blue color are arranged along the edge. A picnic area with tables and chairs is also visible, along with a children's play area nearby.

Home in Lovettsville

4.83 out of 5 average rating, 108 reviews

Cozy 3500sf Private 10ac. pickleball-hot tub-pool

5/6 (6th bedroom has queen sofa bed) Bedrooms furnished w/linens and all your needs 10 private acres in Farm land views of horses Remodeled fully equipped Kitchen w/new appliances 5 full baths w/spa like showers 7 person hot tub 35,000 gallon in ground private pool opens May 25 Private Tennis Court (basic)/Basketball Court 2 Fire pits Picnic area with grills and patio furniture Kiddos play area w/swing sets and slides Large great room/family room 10 acres with 4 acres a forest Dining for 8+

Guest favorite

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

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 favorite

A charming stone cottage is set against a backdrop of lush trees and open sky. A gravel path leads to the entrance, with two chairs positioned on the grassy area, offering a serene view of the surrounding nature.

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

A spacious waterfront house is shown surrounded by lush trees, with multiple balconies and large windows. A sandy area extends toward the water's edge, and smooth stones form a barrier along the shore, reflecting the natural beauty of the Chesapeake Bay.

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 favorite

Cottage in North Beach

4.98 out of 5 average rating, 150 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 favorite

A covered patio area features a decorative table surrounded by chairs, offering views of the lush green lawn and the water. A variety of plants and trees frame the scene, creating a serene outdoor space perfect for relaxation.

Apartment 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 favorite

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 favorite

A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.

Cottage in Pasadena

4.97 out of 5 average rating, 173 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Top guest favorite

A wooden dock extends over still waters, bordered by tall grasses and reeds. A red boat and a small blue boat are tied to the dock, reflecting in the calm water. Mist envelopes the background, softening the view of distant homes and boats.

Place to stay in Annapolis

4.94 out of 5 average rating, 121 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

*Hot tub* “Chesapeake Bay View Paradise" (3BR/2BA Penthouse Suite). Private penthouse level of a 2-level duplex, new deck, gorgeous Chesapeake Bay views, steps to sandy beach. 3 car parking. Gourmet kitchen, SS appl, granite counters, bar. Comfy living & dining areas. Entry handrail installed 9/20/24. 2 King BR, 1 Queen BR + Queen sleeper sofa in living area. Sleeps 8. 2 spa inspired baths, 1 jetted 2-person Jacuzzi tub inside. Outdoor Spa with Jets * Best Places To Stay Annapolis

Guest favorite

A wooden dock extends over calm waters, featuring four Adirondack chairs arranged facing the serene view. A light casts a soft glow on the water's edge, and the distant shoreline is lined with trees and structures, hinting at nearby activity.

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!

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Olney vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Olney's top sights

The Adventure Park at Sandy Spring7 locals recommend

The Brookeville Beer Farm7 locals recommend

Panera Bread8 locals recommend

Safeway6 locals recommend

Mamma Lucia6 locals recommend

Lone Oak Farm Brewing Company8 locals recommend

Other great vacation rentals in Olney

Guest favorite

A modern kitchen space is highlighted by a white countertop and sleek cabinetry. Bar stools are positioned at the kitchen island, and appliances are integrated into the design. Soft lighting accentuates the area, creating a bright and clean environment.

Apartment in Georgetown

4.88 out of 5 average rating, 121 reviews

Cozy Modern Apt. In G-Town

Guest favorite

A serene swimming pool is featured in a private outdoor area, surrounded by a stone deck. Two white lounge chairs are positioned nearby, with trees providing a shaded atmosphere. The clear water glistens under a partly cloudy sky, inviting relaxation.

Home in Edgewater

4.92 out of 5 average rating, 143 reviews

House in Edgewater Maryland

Guest favorite

A custom-built residence is presented with a blend of stone and wood accents. Large windows illuminate the inviting front porch, surrounded by manicured landscaping and a lush green lawn. The two-story structure is set against a backdrop of trees, offering a sense of privacy.

Home in Annandale

4.94 out of 5 average rating, 18 reviews

Family Ready Dogs OK Ping Pong Backyard EV Charger

Superhost

A spacious living area features a large sectional sofa positioned around a coffee table, with a geometric area rug beneath. A flat-screen TV is mounted on the wall, and natural light streams in through large windows, enhancing the open layout that flows to the dining area.

Home in Pasadena

4.86 out of 5 average rating, 58 reviews

Beautiful Home Near Beach and Patapsco River

Superhost

A rooftop terrace features six brightly colored blue chairs arranged around a small table, with expansive views of the water and cityscape beyond. The deck is made of light wood planks, and the clear sky enhances the vibrant scene.

Townhouse in Fells Point

4.96 out of 5 average rating, 137 reviews

Artsy, Historic Rowhouse with Striking Harbor Views

Guest favorite

A balcony view is captured at night, featuring two chairs and a small table. A grill is positioned on one side, and string lights are softly glowing, creating a relaxed ambiance. The city's skyline and street lights are visible in the background.

Condo in Bethesda

4.9 out of 5 average rating, 191 reviews

Bright 2br w amazing loc and view

Top guest favorite

The exterior of the house is showcased with a charming wrap-around porch, flanked by neatly trimmed landscaping. A three-story structure features shingle siding and multiple large windows that allow ample natural light. The front entrance is accessed via a set of stone steps.

Home in Arlington

4.97 out of 5 average rating, 103 reviews

Entire family size house steps to ANC & metro walk

Superhost

Home in Germantown

4.8 out of 5 average rating, 56 reviews

Sophia’s victorian

Show all

Quick stats about vacation rentals in Olney

Total rentals
20 properties
Total number of reviews
570 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace
Local attractions
Olney Theatre Center, Safeway, and Harris Teeter

Frequently Asked Questions

How much does it cost to stay in house rentals in Olney?
Experience the best of Olney with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Olney?
Yes! Work meets play with ease at over 10 vacation rentals in Olney featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Olney have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Olney. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Olney?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Olney

Top-rated vacation rentals in Olney

Vacation rentals for every style

Popular amenities for Olney vacation rentals

Stay near Olney's top sights

Other great vacation rentals in Olney

Quick stats about vacation rentals in Olney

Total rentals

Total number of reviews

Rentals with dedicated workspaces

Wifi availability

Popular amenities

Local attractions

Frequently Asked Questions

Destinations to explore