Vacation rentals in Friendship

4.98 out of 5 average rating, 157 reviews

Farm stay in Accokeek

Frolic Fields: A Woodsy 14 Acre Homestead w/ Sheep

Easily escape to the woods on a 14 acre homestead that's only 20 miles from DC. Surrounded by the forest with amazing views, designed by artists, this secluded hideaway is a celebration of Nature and Art. Recharge amongst these ancient trees and all the singing critters that soundtrack the night. Enjoy a fire, frolic in the fields, read on a hammock, strum a guitar, and feel the pressure of modern life melt away. Explore the many bucolic trails nearby. Perfect for retreats and workshops.

Apartment in Upper Marlboro

4.95 out of 5 average rating, 135 reviews

DC Oasis- hot tub, pool, theater/game rm, & more

Have fun and relax at this stylish oasis! Packed w/ amenities. Huge Pool w/multiple cabanas, HOT TUB, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room and outdoor projector too, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Basement apt so there is some movement noise. Updated bath and an outdoor shower. 20 mins from Downtown DC & 6Flags.

4.9 out of 5 average rating, 102 reviews

Cottage in North Beach

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

4.96 out of 5 average rating, 199 reviews

Townhouse in North Beach

Walk to Beach! King Bed & Free Beach Passes

Welcome to Bay Haven at A Haven Away! Relax in a fully-equipped, plant-filled oasis with a king bed primary suite that our guests love. Its prime location is in walking distance to the beach, restaurants, fresh seafood, and wetlands. We’ll share our beach passes and lots of local recommendations so you can enjoy our little slice of heaven. 12 min walk to the beach, boardwalk, restaurants, and kids play areas in cute North Beach, MD 7 min drive to Herrington Harbor 14 min drive to Tacaro Estate

5 out of 5 average rating, 142 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

4.96 out of 5 average rating, 131 reviews

Apartment in North Beach

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

4.94 out of 5 average rating, 163 reviews

Cottage in North Beach

Club Carp North Beach - Steps to the Bay!

Calendar open for bookings in April 2025! Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with 3 bedrooms and 2 full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced side yard with swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars.

4.98 out of 5 average rating, 124 reviews

Home in West River

Cozy waterview home in West River!

Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!

4.99 out of 5 average rating, 214 reviews

Home in Tracys Landing

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

Guesthouse in Stevensville

4.99 out of 5 average rating, 279 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.

4.99 out of 5 average rating, 145 reviews

Home in Deale

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Make wonderful memories. Great place for families and multi family groups.

Guest suite in Chesapeake Beach

4.96 out of 5 average rating, 115 reviews

Nice Guest Suite at Chesapeake Bay

Take it easy at this unique and tranquil getaway. Come and relax in our modern & comfortable guest suite to enjoy a small-town quiet setting with amazing Chesapeake Bay views. A short drive from Washington DC (45 min), Annapolis (30 Min), or Baltimore (1 hr). Groceries, boardwalks, restaurants are all within walking distance. Enjoy cable TV, high-speed Internet, and strong wifi through Xfinity.

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Other great vacation rentals in Friendship

5 out of 5 average rating, 7 reviews

Comfy King Bed Home, walk to dinner & beach!

EmilyRating, 5 stars1 week ago

This is a newly renovated gem, walkable to North Beach boardwalk. Spotless and great outdoor area. Host was very responsive and we would highly recommend. The beach is super close to the DC metro area (one hour) and perfect for young kids since the water is calm, warm, and most importantly shallow. We’ll be back!

Home in Chesapeake Beach

4.92 out of 5 average rating, 154 reviews

Artists amazing sunrise water retreat!

KarolineRating, 5 stars20 months ago

The artist beach house provided a much needed reset time away from home to create uninterrupted for this artist mom. The light on the bay was amazing and mesmerizing to watch change throughout the day. The movement of the waves provides inspired expressive input for mark making and brushstrokes. Brownie beach was fun to beach comb and meet friendly locals too. I had clear skys most night so the star gazing was incredible. You are just steps from the residential boardwalk so you can stretch your legs between art making sessions. If you encounter an artist block there is an extensive collection of books and movies to inspire you. The hostess was attentive and provided daily treats and check ins . I felt safe and cared for on my solo artist retreat.

5 out of 5 average rating, 3 reviews

Waterfront Lux Cottage With Amazing Views Near DC

HeatherRating, 5 stars5 days ago

If you're a family with young kids this is 100% the place for you to stay! Tons of toys and touches that made the place feel welcoming of kids. The house is great for anyone though, beautiful view of the bay. Nice back patio area and just felt like you're staying at your families bay house! North beach is a 3 minute drive and the market down the street was nice also! Will and Loyal are great hosts and communicate quickly!

Guest suite in Upper Marlboro

4.62 out of 5 average rating, 60 reviews

Guest Suite w/ Private Entrance in Upper Marlboro

HunterRating, 5 stars2 weeks ago

My girlfriend and I stayed 2 nights for a concert at the Northwest stadium about 15 minutes away. The place is worth the price for a short trip. Very quiet neighborhood and easy to park.

5 out of 5 average rating, 3 reviews

Sea La Vie

Susan R.Rating, 5 stars5 days ago

What a great stay! Everything is so close! DC is not far and the city around is within driving distance, making for a wonderful stay, can't recommend it enough!

4.83 out of 5 average rating, 106 reviews

Guesthouse in Bowie

Renovated Basement with Private Entrance

AprilRating, 5 stars1 week ago

We had a wonderful stay at this Airbnb! The unit was spotless—everything was incredibly clean and well-maintained, including the bathroom. The space itself was cozy and inviting, and we felt right at home, especially in the living room where we spent most of our time relaxing. The host was very responsive and thoughtful—every detail was well considered, and we truly didn’t need for anything. A nice touch was the complimentary water and sodas, which we appreciated after a long trip. One feature we especially liked was the lighting. The lights operated on what we believe were motion sensors, turning on and off automatically. This was both convenient and energy-efficient, especially if we happened to fall asleep with the lights on—they’d shut off on their own. Overall, it was a comfortable and seamless experience. We would absolutely stay again!

Guest suite in Dunkirk

5 out of 5 average rating, 4 reviews

Pool-side chickens between D.C. and Chesapeake Bay

RyanRating, 5 stars1 week ago

Great stay for our large family! Booked for pool, and we swam every day! Also my kids thoroughly enjoyed the Atari! Was great getting to meet Luis and Laura and their son! Talked about booking next year!