Holiday Rentals in Easton, MD

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Easton, MD holiday rentals
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Best Holiday rentals and Airbnb offers in Easton, MD

Best family friendly Easton, MD holiday rentals

Among the 21 accommodations in Easton, MD, here are the 4 best family friendly rentals

Travelers Rest Spacious 5br Pool Riverfront Pier Charming Easton Saint Michaels - Easton, MD
8.8 6 reviews
Easton, MD
17/09 – 20/09
SG$1715/nighttotal: SG$5145 (3 )

Travelers Rest Spacious 5br Pool Riverfront Pier Charming Easton Saint Michaels

5 2
apartment , Easton
This Easton holiday home, situated within 14.5km of St. Michaels, the Talbot County Historical Society, and the Avalon Theatre, offers convenient access to local attractions.
Sleeping up to 10 guests, this five-bedroom property boasts four bathrooms, a fully equipped kitchen including a dishwasher and microwave, a swimming pool, parking, and modern amenities such as a smart TV and barbecue grills; pets are welcome.
True In-town St Michaels 6 Acre Waterfront - Heated Pool - Easton, MD
10 190 reviews
Easton, MD
17/09 – 20/09
SG$2276/nighttotal: SG$6828 (3 )

True In-town St Michaels 6 Acre Waterfront - Heated Pool

5 2
apartment , Easton
The Spencer Creek Cabin is situated just outside of Historic Downtown Saint Michaels, a 5-10 minute bike ride away, with a grocery store, petrol station and coffee shop across the street. The cabin has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The property has five bedrooms, three bathrooms and a floor area of 279 square metres, comfortably accommodating up to eight guests. Amenities include a private swimming pool, a hot tub, a tennis court, a garden, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay.
Minutes From Downtown Easton And St. Michaels | Pool | Kayaks | Private Dock - Easton, MD
10 17 reviews
Easton, MD
17/09 – 20/09
SG$2616/nighttotal: SG$7848 (3 )

Minutes From Downtown Easton And St. Michaels | Pool | Kayaks | Private Dock

5 2
apartment , Easton
This luxurious Easton, Talbot County, Maryland waterfront estate boasts 800 feet of Miles River frontage, a private dock, kayaks, and paddleboards, and is conveniently located for day trips to Annapolis and St. Michaels.
This five-bedroom, six-bathroom property sleeps ten guests and features a gourmet kitchen, multiple fireplaces, a recreation room with games, a private pool (open 15 May to 15 October), and extensive grounds including a koi pond and fire pit, offering ample space for relaxation and entertainment.
Minutes From Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly - Easton, MD
9.6 40 reviews
Easton, MD
08/08 – 24/08
SG$892/nighttotal: SG$14272 (16 )

Minutes From Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

3 2
apartment , Easton
This charming apartment is located in St. Michaels, just a short drive from the Bay Hundred Community Pool, golf courses, and the town centre. It has received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The apartment is spacious, covering 196 square metres and comfortably accommodating up to 6 guests in its 3 bedrooms and 3 bathrooms. You can enjoy a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a spa, and parking, as well as access to the internet.

Best Easton, MD holiday rentals with parking

Minutes From Downtown Easton And St. Michaels | Pool | Private Dock | Luxury - Easton, MD
10 1 review
Easton, MD
08/08 – 24/08
SG$3005/nighttotal: SG$48080 (16 )

Minutes From Downtown Easton And St. Michaels | Pool | Private Dock | Luxury

5 2
apartment , Oxford
This five-bedroom house, ideal for families, is located in Royal Oak, Maryland, approximately 15km from Saint Michaels Village and its museums, and within 20km of the Chesapeake Bay Maritime Museum and Saint Mary's Square.
The 632 square metre property boasts a private pool, fitness centre, tennis court, and spa, accommodating up to 10 guests and offering a fully equipped kitchen, free Wi-Fi, and ample parking.
Bay Breeze - Easton, MD
Easton, MD
17/09 – 20/09
SG$1782/nighttotal: SG$5346 (3 )

Bay Breeze

1 2
house , Grasonville
Bay Breeze, situated in Grasonville, Maryland, is approximately 27 kilometres from Sandy Point State Park and 40 kilometres from Annapolis.
This three-bathroom, five-bedroom property offers 327 square metres of space, accommodating up to 19 guests and boasting a private pool, free Wi-Fi, and free private parking; explore Grasonville's attractions or enjoy the house's amenities.
Sunset Shores | An Esvr Property - Easton, MD
Easton, MD
17/09 – 20/09
SG$2181/nighttotal: SG$6543 (3 )

Sunset Shores | An Esvr Property

4 2
apartment , Oxford
This waterfront property in Royal Oak, a short drive from St. Michaels, offers direct access to Bridge Creek with a dock and is located approximately 4.5 kilometres from the Chesapeake Bay Maritime Museum.
This family-friendly holiday home accommodates up to 8 guests with 4 bedrooms and 3 bathrooms, featuring a private saltwater pool (seasonal), kayaks, a 1.6-hectare yard with a basketball hoop, and a great room with a fireplace.
Kent Island Waterfront | Pool | Outdoor Dining | Stunning View | Private Dock - Easton, MD
8.0 7 reviews
Easton, MD
17/09 – 20/09
SG$1898/nighttotal: SG$5694 (3 )

Kent Island Waterfront | Pool | Outdoor Dining | Stunning View | Private Dock

5 2
apartment , Grasonville
This Grasonville waterfront property is situated approximately 14.5 kilometres from Queenstown Premium Outlets and Queenstown Harbour Golf Links, offering stunning Chesapeake Bay views.
This 327 square metre house boasts five bedrooms, three bathrooms, sleeps ten guests, and includes a private pool, tennis court, spa, and fully equipped kitchen; nearby attractions include the Chesapeake Bay Environmental Centre.

Frequently asked questions about holiday rentals in Easton, MD

  • What are some interesting places to visit in or near Easton, MD?

    Easton is a charming town with plenty to see. The historic district is a must-visit, with beautiful architecture and quaint shops. The Chesapeake Bay Maritime Museum is a great place to learn about the area's maritime history. For a day trip, you can head to St. Michaels, a picturesque town on the Eastern Shore, about 20 minutes away.
  • What are the best Airbnb and vacation rentals in Easton, MD?

    Chill In The Crib Easton - Maryland, Econo Lodge Easton Route 50 and Tranquil Easton Waterfront Property (Hot Tub&pool) are the most popular Airbnb and vacation rentals in Easton, MD among travelers.

  • Which walking or cycling routes are the best in Easton, MD?

    The scenic waterfront trail along the Choptank River is a popular choice for both walking and cycling. It's a lovely, flat route that's perfect for a leisurely stroll or a brisk bike ride. The town also has several other walking and cycling routes, including the Easton Greenway, which winds through the town's parks and residential areas.
  • What are the most popular Airbnbs in Easton, MD?

  • What sports or outdoor activites can visitors enjoy in and around Easton, MD?

    Easton is a great place for outdoor enthusiasts. You can enjoy kayaking, canoeing, and paddleboarding on the Choptank River. There are also several golf courses in the area, including the Easton Country Club. The town also hosts a variety of sporting events throughout the year, such as the annual Easton Marathon and the Chesapeake Bay Challenge.
  • What are the best vacation rentals with a pool in Easton, MD?

  • What other towns or cities can be easily accessed from Easton, MD?

    Easton is conveniently located near other interesting towns and cities. Annapolis, the state capital of Maryland, is about an hour's drive away. You can also easily reach the Eastern Shore towns of St. Michaels, Oxford, and Cambridge, all of which offer unique attractions and experiences.
  • What are the best rentals for families and kids in Easton, MD?

  • What amenities are commonly available in vacation rentals in Easton, MD?

    Vacation rentals in Easton typically offer a range of amenities, including fully equipped kitchens, comfortable bedrooms, and laundry facilities. Many also feature outdoor spaces like patios or balconies, and some even have swimming pools or hot tubs. You can find rentals that suit different needs and budgets.
  • What are the best rentals or Airbnbs with a jacuzzi in Easton, MD?

  • What time of year is best to rent a vacation rental Easton, MD?

    The best time to visit Easton depends on your preferences. Spring and autumn offer mild weather and beautiful foliage. Summer is popular for outdoor activities, while winter is quieter and offers a chance to enjoy the town's charming atmosphere.
  • What are the local dishes in Easton, MD region?

    The Eastern Shore is known for its fresh seafood, so you'll find plenty of restaurants serving up delicious crab cakes, oysters, and other local specialties. You should also try the region's famous Smith Island cake, a layered dessert with a rich history.

Destinations nearby

Best Easton, MD holiday rentals with a balcony

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Easton, MD
Easton, MD
08/08 – 24/08
SG$374/nighttotal: SG$5984 (16 )

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

4 2
house , Trappe
This spacious holiday home is located in Trappe, just 5.5 miles from the Academy of the Arts and 25 miles from Federalsburg Marina, offering a tranquil escape in a charming town with a rich history. The property spans 204 square metres and comfortably accommodates up to 8 guests, providing ample space for families or groups.
The house is fully equipped with modern amenities including a kitchen with a fridge, microwave oven, and dishwasher, a private outdoor pool and gazebo, air conditioning, and free Wi-Fi. Guests can also enjoy a dedicated outdoor dining area, a washing machine, and parking.
Downtown St. Michaels | Porch + Pet-friendly - Easton, MD
Easton, MD
26/07 – 01/08
SG$907/nighttotal: SG$5442 (6 )

Downtown St. Michaels | Porch + Pet-friendly

1 2
apartment , Easton
This studio flat is located in the central district of St. Michaels, a mere 100 metres from its boutiques, seafood restaurants, and harbour, offering authentic historic charm with exposed wood beams and coastal décor.
This pet-friendly accommodation for two guests features a kitchenette with a fridge and microwave, air conditioning, a private terrace, and dedicated parking, with keyless entry for convenience.
Harbor View Suite\ntalbot County License Number Strn-25-58 - Easton, MD
10 77 reviews
Easton, MD
26/07 – 01/08
SG$454/nighttotal: SG$2724 (6 )

Harbor View Suite\ntalbot County License Number Strn-25-58

1 2
apartment , Easton
This Saint Michaels suite, a short walk from the Chesapeake Bay Maritime Museum and the St. Michaels Museum, offers stunning harbour views and proximity to Lyons Distilling Company within the Old Mill complex.
The 45-square-metre apartment includes a king-size bed, sofa, and a kitchenette with a fridge, freezer, microwave, and coffee makers, accommodating two guests and featuring a private bathroom and off-street parking.
Chesapeake Bay Waterfront Retreat With Private Pool! The Shore At It's Best! - Easton, MD
10 28 reviews
Easton, MD
17/09 – 20/09
SG$2070/nighttotal: SG$6210 (3 )

Chesapeake Bay Waterfront Retreat With Private Pool! The Shore At It's Best!

5 2
apartment , Grasonville
This luxurious waterfront property near Grasonville offers stunning views and is situated 14.5 km from Queenstown Premium Outlets and Queenstown Harbour Golf Links, and 19.3 km from the Hazel Miner Monument and Wye Oak State Park.
This spacious 446-square-metre five-bedroom residence sleeps twelve, boasting a private pool, jacuzzi, tennis court, and a fully equipped kitchen, plus an on-site games room for family entertainment.

Best pet friendly Easton, MD holiday rentals

Among the 21 accommodations in Easton, MD, here are the 4 best pet friendly rentals

Furnished Very Spacious - Easton, MD
10 5 reviews
Easton, MD
08/08 – 24/08
SG$246/nighttotal: SG$3936 (16 )

Furnished Very Spacious

1 2
apartment , Trappe
This Trappe apartment, situated midway between Easton and Cambridge, Maryland, offers convenient access to the Chesapeake Bay and local amenities.
The one-bedroom, one-bathroom flat sleeps two guests, includes Wi-Fi, parking, and air conditioning, and welcomes pets (a £240 non-refundable fee applies).
Minutes From Downtown St. Michaels | Pool | Hot Tub | Private Dock - Easton, MD
8.0 2 reviews
Easton, MD
17/09 – 20/09
SG$1817/nighttotal: SG$5451 (3 )

Minutes From Downtown St. Michaels | Pool | Hot Tub | Private Dock

4 2
apartment , Tilghman Island
This waterfront flat is located in St. Michaels, Talbot County, just a short distance from the Chesapeake Bay Environmental Center and Matapeake State Park, offering a peaceful escape from the hustle and bustle. The flat is situated in a tranquil rural setting, close to local attractions such as the St. Michaels Museum and the Chesapeake Bay Maritime Museum.
The spacious four-bedroom flat, covering 184 square metres, comfortably accommodates up to eight guests. This property offers a range of amenities including a private pool and hot tub, a well-equipped kitchen, and a large outdoor deck, perfect for relaxing and enjoying the beautiful surroundings.
Private Boat Dock! Wye River Retreat In Queenstown - Easton, MD
10 2 reviews
Easton, MD
17/09 – 20/09
SG$2342/nighttotal: SG$7026 (3 )

Private Boat Dock! Wye River Retreat In Queenstown

5 2
apartment , Grasonville
This Grasonville waterfront vessel is situated near the Pickering Creek Audubon Center and Chesapeake Bay Maritime Museum, offering convenient access to kayaking and other water activities.
This 418-square-metre luxury houseboat boasts five bedrooms, five bathrooms, a fully equipped kitchen, a private swimming pool, and can accommodate up to ten guests, making it ideal for families or groups.
Ferry Bridge House - Easton, MD
10 8 reviews
Easton, MD
17/09 – 20/09
SG$1921/nighttotal: SG$5763 (3 )

Ferry Bridge House

1 2
apartment , Easton
This four-bedroom apartment is situated on a private peninsula on the Miles River, just a short drive from the historic towns of Easton and St Michaels. The property offers a secluded location with stunning water views, a spacious living area, a fully equipped kitchen with a dishwasher, and a private garden, ideal for a group of up to six guests.
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