Vacation rentals in Cheltenham

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cheltenham

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Guest suite in Bowie

4.94 out of 5 average rating, 336 reviews

Beautiful Bsmt. Suite, Quiet, Upscale Neighborhood

A luxurious, beautiful, and spacious basement suite designed exclusively for guests with a private sliding door entrance. Features include a large living room, two bedrooms, bathroom, playroom, Kitchenette. Wi-Fi, Smart TV, patio, and standby generator. 30 minutes from BWI or Reagan National Airports and 5 miles to Metro & MARC station, this is a commuter's dream. Close to shopping and a short drive to FedExField – Washington Redskins Stadium, Six Flags, Washington DC & MGM National Harbor.

Oct 3 – 10

G$23,962 GYD per night

Guest favorite

Guest suite in Brandywine

5.0 out of 5 average rating, 10 reviews

1 bdrm Lux Suite & Retreat Minutes from Wineries

Kick back and relax in this calm, stylish space. This is a 1 bdrm Loft Style Private Basment with a bathroom, wetbar, and entrance. This location is on an exclusive 5-acre retreat that's tucked way and surrounded by beautiful nature. There is a lovely outdoor area, including waterfall, pond, firepit, and seating areas around the property. Enjoy a quick getaway/retreat or even a quiet work from home space only minutes from over 4 local wineries, Patuxent River, & 30 min from DC/ National Harbor.

Oct 7 – 14

G$23,222 GYD per night

Guest favorite

Apartment in North Beach

4.97 out of 5 average rating, 102 reviews

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.

Mar 7 – 14

G$27,341 GYD per night

Guest favorite

Guest suite in Waldorf

4.88 out of 5 average rating, 68 reviews

Cheerful1 bedroom basement with separate entrance

Take it easy at this unique and tranquil getaway. Keeping it simple and clean at this peaceful and centrally-located place. Cozy and placed in a beautiful quiet neighborhood. one bedroom Suite with its own bathroom and private side entrance provides a relaxing atmosphere for work or vacation. No shared spaces. No keys needed . it's a keyless secure entrance. There is no kitchen, however, the Suite includes fridge, microwave, keurig coffee machine with included coffee pods, cups and air fryer.

Feb 19 – 26

G$21,774 GYD per night

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 206 reviews

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.

Jul 14 – 21

G$20,406 GYD per night

Guest favorite

Guest suite in Fort Washington

4.94 out of 5 average rating, 113 reviews

Near National Harbor/MGM Casino/COZY Studio Suite

✔2 guests MAX. NO EXCEPTIONS (NO GATHERINGS, NO PARTIES , NO EVENTS) ✔ 100% ID required for New Airbnb Guests with less than 2 reviews. ✔Small & Cozy space: 300 sq ft (Refer to the pics) ✔Private & separate entrance ✔Quiet residential neighborhood of single-family homes ✔Reserved parking for 1 vehicle ✔10 mins from MGM Casino/National Harbor ✔20-mins drive to Washington, D.C. ✔1 Pet welcome ✔1 queen-size bed ✔2 TVs ✔Kitchenette - Hot plate (no stove) ✔K-Cups machine ✔Towels, shower gel,

May 13 – 20

G$18,268 GYD per night

Guest favorite

Apartment in Bowie

4.98 out of 5 average rating, 117 reviews

Couple's Retreat - Private Entrance Basement Apt

Gem! This open and airy basement apartment is great for a weekend getaway or a longer stay -- all the comforts of home. It contains a fully equipped kitchen, living room with large sectional, TV and electric fireplace, dining area, bedroom with queen bed, a nook with sleep sofa, full bath, and washer/dryer. Private entrance with patio and a zen koi pond garden! Couples, travel nurses, and other medical professionals love this private apartment close to hospitals and health facilities.

May 29 – Jun 5

G$24,448 GYD per night

Guest favorite

Home in Temple Hills

4.84 out of 5 average rating, 140 reviews

DC MGM National Harbor Modern House with backyard

Welcome to this calm, stylish, cozy, private space where you can relax and enjoy your special moments. 20 min away from the Capitol Downtown DC, 10 minutes away from MGM and National Harbor and 5 minutes away from Andrew Airforce Base. Free parking and amenities competing a luxury hotel. Split level, 2 bedroom, 2 bathroom townhouse with a large backyard, patio, build in out door grill. Lots of free parking. Your pets are welcome. Allow me to enhance your experience.

Aug 12 – 19

G$33,064 GYD per night

Guest favorite

Guest suite in Upper Marlboro

4.95 out of 5 average rating, 104 reviews

Private Apartment on a Horse Farm

My place is convenient to Joint Base Andrews (20 minutes), Washington DC and Annapolis MD (both are about 40 minutes by car) but you’ll love my place because of the outdoor space and the peace and quiet. For Equestrians, we are within 10 minutes of the Prince George's Equestrian Center as well. My place is good for couples, solo adventurers, families (with kids), and well-behaved pets. With a full-sized kitchen, this apartment is a great home away from home.

Jul 11 – 18

G$20,021 GYD per night

Guest favorite

Guest suite in Waldorf

5.0 out of 5 average rating, 13 reviews

Chocolate Bliss-Inn (King Size Bed)

Forget your worries in this spacious and serene space. Chocolate Bliss-Inn features a full size bedroom with king size bed, full bathroom, informal living room area brown leather sectional and table. Kitchenette includes refrigerator, induction two plate cook top, wet bar with granite countertop pendant and recess lighting. Close to Washington DC, Virginia, National Harbor, Tanger Outlets, all shopping and eateries within the Charles County area.

May 10 – 17

G$18,017 GYD per night

Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 538 reviews

“Cabana by the Bay”-tiny home on a pier!

This tiny home is a newly renovated cabana sitting on a pier. Fall asleep to the sound of waves crashing under you! Enjoy shared use of our private beach. Kayaks and bikes are available April-October and are stored directly across the street. Go crabbing or fishing off the pier and walk to one of the many nearby restaurants. Check out the summer concert series at the Calvert Marine Museum.

Oct 23 – 30

G$29,757 GYD per night

Guest favorite

Guest suite in 6, Waldorf

4.87 out of 5 average rating, 84 reviews

Brand New!! 1 Bedroom In-law suite

Brand new charming apartment in a quiet neighborhood off of Marshall Corner Road. Owners live upstairs. You have your own entrance into the basement apartment. Close to the National Harbor, DC, and Andrews Air Force Base. Only minutes from shopping and restaurants. Come visit many historical sites in Charles County.

Jun 18 – 25

G$10,565 GYD per night