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Apartment holiday rentals in Saint Michaels

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Top-rated apartment rentals in Saint Michaels

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

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Guest favourite
A cozy living area features a dark leather sofa and two blue chairs arranged around a round coffee table. Soft lighting is provided by stylish lamps on both ends. Framed artwork lines the walls, and natural light streams through the curtains.
Flat in Cambridge
4.9 out of 5 average rating, 153 reviews

Little Slice of Cambridge. 2 bedroom, pet friendly

You’ll be staying right in the center of the Historic district, close enough to walk to town and enjoy shopping or some of the great restaurants. Just two blocks from the water, a short stroll to the lighthouse or down to the water front and enjoy the park. This newly listed 2 bedroom , pet- friendly apartment has everything you will need to explore the history, food and waterfowl found in this area. Park your boat here. We can’t wait for you to experience Cambridge and relax in the “West End”.

Top guest favourite
Flat in Baltimore
4.98 out of 5 average rating, 527 reviews

Butchershill-Clean, KingBed, Parking, next to Park

My name is John S Marsiglia. Always clean, very comfortable New King Mattress, 100feet to beautiful park, Warm & Cozy Fireplace, Self checkin , Historic 2207 E Baltimore St. Search online. 900 Sq Ft. 12 ft ceilings,Fully equipped kitchen/kitchenette,Coffee,Tea,Cream,Brita filtered water pitcher,50" TV, streaming , free Prime tv ,top speed WiFi, surround sound, comfortable clean furniture, antiques, oriental rugs, workspace w/desk, beautiful bathroom, dual shower heads&seats, private full laundry

Top guest favourite
A bright dining area features a wooden table surrounded by four chairs, illuminated by natural light from the sliding glass doors. A cozy armchair with a soft throw blanket is present, with a clock and decorative art pieces on the walls, creating a welcoming atmosphere.
Flat in Church Creek
4.97 out of 5 average rating, 446 reviews

Nature's Rest in Church Creek

Nature's Rest is located just minutes from Blackwater Wildlife Refuge, The Harriet Tubman Museum, Blackwater Adventures! Boat ramps are close by for easy access to the Chesapeake Bay and its tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

Top guest favourite
A serene view of the Chester River is presented, with soft pink clouds reflecting the sunset hues. Docked boats are visible along the wooden dock, while lush greenery frames the scene, providing a peaceful atmosphere at twilight.
Flat in Grasonville
4.9 out of 5 average rating, 227 reviews

Halcyon house. Lovely views on MD eastern shore.

This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to several restaurant

Top guest favourite
A modern living area features a light-colored sofa adorned with a teal throw blanket. A round wooden table accompanied by metal chairs is positioned nearby. A decorative mirror and an abstract painting are displayed on the wall, while a stone fireplace adds a subtle touch of warmth.
Flat in Stevensville
4.98 out of 5 average rating, 307 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Top guest favourite
Flat in Saint Michaels
4.92 out of 5 average rating, 222 reviews

Charming Studio in the heart of St. Michael's, MD.

Welcome to Lucky Ducks Studio! Enjoy a fully renovated furnished studio in the heart of St. Michael's, MD. Located on Talbot Street in the historic 1850’s McMillian House, the 2nd floor studio offers couples a cozy "British" style experience that sleeps 4 (queen bed & sofa that transitions to queen), a full bath with a claw tub and a gorgeous industrial style kitchen. Your steps away from the Miles River, shopping, museums, restaurants, breweries and wineries. Free WIFI and YouTube TV.

Top guest favourite
Flat in Chestertown
4.97 out of 5 average rating, 279 reviews

Secluded and romantic getaway in Chestertown

Escape to a secluded studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of private gardens. Relax in front of the fire with views of gardens in the windows. Kitchenette has large toaster oven, hot plate, microwave, fridge, and Keurig/drip coffee makers. We have an under counter filtration system for pure delicious drinking water. King bed with deluxe linens and mattress, washer dryer. We also host ‘Wren Retweet”, a 5 bedroom house by the carriage house.

Top guest favourite
A bright yellow building features large blue shutters and a welcoming entrance. A sign is placed outside, and vibrant flowers border the steps. In the background, another structure is visible, along with flags proudly displayed.
Flat in Saint Michaels
4.97 out of 5 average rating, 144 reviews

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

Guest favourite
A spacious living area is highlighted by large angled windows, allowing natural light to fill the space. A comfortable sectional sofa is complemented by a coffee table, while a kitchenette is visible in the background. An attached image shows a private outdoor deck with seating.
Flat in Northeast Washington
4.98 out of 5 average rating, 294 reviews

Luxury escape in DC now with a private Deck!

History and luxury meet in your rental which is a meticulously renovated luxury floor which includes top of the line amenities, private rooftop deck with Pergola, dual sided gas fireplace, luxurious and spacious bathroom including washer dryer, solar powered black-out blinds and leading gourmet coffee machine! We are close to Capital Hill, Brookland, Ivy City, Union Market, & H street corridor and a 10 minute Uber ride from Union Station. Free parking is provided onsite!

Top guest favourite
A red umbrella provides shade over a square table with a glass top, accompanied by two cushioned chairs. Lush green grass surrounds the seating area, framed by tall trees and distant views of the water, creating a serene outdoor space.
Flat in Port Republic
4.96 out of 5 average rating, 245 reviews

Serenity Suite on Chesapeake Bay

Come enjoy our waterfront home on the scenic Calvert Cliffs. Take in beautiful Bay views in Adirondack chairs with stunning vistas. Photograph wildlife. Comfortable ½ mile walk to private community bay shoreline. Have breakfast in the yard while enjoying the sunrise. Stroll the community shoreline and explore fossil hunting, hike at nearby trails. No pets are allowed because I have a severe allergic reaction to pet hair and dander. Thanks for your understanding.

Top guest favourite
A serene view of the St. Mary's River is framed by a white awning. Calm waters reflect the clear blue sky and a single sailboat is visible in the distance. Lush greenery lines the far shore, enhancing the peaceful atmosphere.
Flat in Lexington Park
5 out of 5 average rating, 399 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here year around! SUNSETS!

Top guest favourite
Flat in Annapolis
4.9 out of 5 average rating, 100 reviews

Charming, Chic Downtown Annapolis Apartment

In the heart of Downtown Annapolis. One block from Main Street/West Street/Church Circle. Close proximity to USNA, Ego Alley, Eastport, State House, shops, galleries, restaurants/bars and all other DTA amenities. This private apartment has an open floor plan and is elegantly decorated (with a modern twist). One Full Bathroom with tiled shower. One Bedroom with walk-in closet (with W/D).

Popular amenities for Saint Michaels apartment rentals

Quick stats about flat rentals in Saint Michaels

  • Nightly prices starting at

    Saint Michaels holiday rentals start at £174 per night before taxes and fees

  • Verified guest reviews

    Over 480 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Saint Michaels rentals

  • 4.9 Average rating

    Saint Michaels stays are highly rated by guests – averaging 4.9 out of 5!

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