Vacation rentals in Cheltenham

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Top-rated vacation rentals in Cheltenham

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Guest favorite

Guest suite in Bowie

4.94 out of 5 average rating, 338 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 9 – 16

G$23,877 GYD per night

Guest favorite

Apartment in Waldorf

4.96 out of 5 average rating, 109 reviews

Waldorf MD: Gingko Lane: MCM Vibe Newly Renovated

Newly Renovated Light airy 1 BR (QN) basement apartment in a single family home in quiet residential neighborhood. We live upstairs. YOUR SPACE IS FULLY PRIVATE & SECURE. PRIVATE KEYPAD ENTRY. LR has 2 sofas & high quality Full air mattress. Perfect for 2 couples or a small family. Modest travel distance from DC metro area and the Potomac Corridor. Washington DC, National Harbor, the Chesapeake Bay, the Northern Neck of VA, and historic sites like Mt Vernon, and Old Town Alexandria are nearby.

May 13 – 20

G$30,623 GYD per night

Guest favorite

Apartment in North Beach

4.96 out of 5 average rating, 104 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.

Oct 16 – 23

G$27,604 GYD per night

Guest favorite

Guest suite in Waldorf

4.84 out of 5 average rating, 70 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.

Jan 12 – 19

G$23,718 GYD per night

Guest favorite

Guest suite in La Plata

4.88 out of 5 average rating, 221 reviews

Beautiful Rural Suite near Washington, D.C.

Enjoy a rural environment only 50 minutes outside of Washington, D.C., and 45 minutes away from Andrew's Air Force Base. Located in a quiet wooded neighborhood with horses, goats, ducks, and more this property allows children space to run and play. Stores are less than 10 minutes down the road. This is a perfect little haven, fully equipped with a kitchen and laundry facilities. Parking is available for boats and trailers. Please Note: Sunday check-in is at 4pm, unless requested otherwise.

Oct 6 – 13

G$23,013 GYD per night

Guest favorite

Cottage in Annapolis

4.94 out of 5 average rating, 316 reviews

Wright’s Cottage, Pets Welcome!

We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large properties and big trees gives one a cozy, country feel, yet so close to bustling Annapolis! There is RV/EV hookup, an outdoor woodstove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your dog, cat, or maybe, pig or rabbit 🤔can freely play. Everything is very laid back at Wright’s cottage. Come stay and take the time to enjoy being you!

Oct 6 – 13

G$31,265 GYD per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 195 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

Apr 19 – 26

G$18,516 GYD per night

Guest favorite

Apartment in Bowie

4.98 out of 5 average rating, 118 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.

Jun 10 – 17

G$24,466 GYD per night

Guest favorite

Home in Temple Hills

4.84 out of 5 average rating, 143 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.

Feb 25 – Mar 4

G$33,638 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 16 – 23

G$20,035 GYD per night

Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 541 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.

Apr 15 – 22

G$29,779 GYD per night

Guest favorite

Guest suite in Upper Marlboro

4.97 out of 5 average rating, 132 reviews

Great Stay! Minutes from Downtown DC & much more!

Home away from home! The newly built townhouse is located close to a variety of restaurants & shopping areas. Just 2.0 miles from Andrews Air Force Base, 2 mins from I-495 Capital Beltway/ I-95, less than 15 miles to downtown DC, less than 10 minutes to the National Harbor, MGM Casinos & FedEx Field.

May 21 – 28

G$18,805 GYD per night