Holiday Rentals Massey from £87: Find Short-Term Rentals & Holiday Accommodations

Q: What are some of the best holiday rentals that Massey has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay : This holiday home rental outside of Massey is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Massey holiday rentals

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

1. Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Riley B.

includes taxes & fees

19 Oct - 20 Oct

A spacious living area with a dining table, sofa, and a kitchen in the background.

2. Newly restored apartment in the heart of Chestertown

Chestertown

Susan A.

includes taxes & fees

12 Oct - 13 Oct

A riverside dock with boats, a covered seating area, and a bridge in the background.

3. Historic Chesapeake City Stay

Chesapeake City

Martha J.

includes taxes & fees

15 Oct - 16 Oct

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

4. First Floor Studio Apartment in Historic Chestertown

Chestertown

"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"

Charr

includes taxes & fees

12 Oct - 13 Oct

A bunk bed room with white bedding and blue throw blankets.

5. Bohemia Manor Farm

Chesapeake City

includes taxes & fees

25 Oct - 26 Oct

A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

6. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

includes taxes & fees

13 Oct - 14 Oct

A house with a covered porch, a grill, and a propane tank in the yard.

7. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Betterton

includes taxes & fees

20 Oct - 21 Oct

A deck with outdoor furniture, a potted plant, and a house in the background.

8. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...

Miriam G.

includes taxes & fees

20 Oct - 21 Oct

A hallway with wooden flooring, a door on the right, and a window at the end.

9. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

includes taxes & fees

3 Nov - 4 Nov

A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

10. Beachcomber Suite

Kent County

"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...

Lisa E.

includes taxes & fees

19 Oct - 20 Oct

A hallway with a dining area featuring a table and chairs, a dark wooden floor, and recessed ceiling lighting.

11. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Chesapeake City

includes taxes & fees

2 Nov - 3 Nov

A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

12. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Dover

Richard B.

includes taxes & fees

20 Oct - 21 Oct

A wooden cabin with a porch, surrounded by dense forest.

13. Country Get Away Studio Apartment

Elkton

JAMES V.

includes taxes & fees

26 Oct - 27 Oct

14. Sunset River Shack -amazing waterfront view

Elkton

Natasha G.

A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

15. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Bear

"My boyfriend and I had a fantastic night on the yacht. We arrived right on time and found the AC and the lights on and ready for our arrival. I sunbathed on the front of the yacht and danced on the back after dinner at Grain H2O. The restaurant is located at the top of the hill on the marina . There was a band and we could hear the music from the boat. The marina was clean and everyone is friendly. At night it was very peaceful and easy to fall asleep. The morning we enjoyed our last couple of...

Karen

includes taxes & fees

12 Oct - 13 Oct

A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

16. Turtle Cove Room

Kent County

includes taxes & fees

19 Oct - 20 Oct

A covered deck area with a grill and outdoor seating.

17. Nature's Haven Tiny Home

Bear

Maxwell

includes taxes & fees

11 Oct - 12 Oct

A two-story residential building with a stone facade, a large front lawn, and a driveway.

18. Elegant Family Stay • Quiet Neighborhood • Comfort

New Castle

Daniel J.

includes taxes & fees

12 Oct - 13 Oct

A swimming pool with a tiled edge, surrounded by potted plants and outdoor furniture.

19. Mini Aruba RV/Glamping Tent

Dover

Robert N.

includes taxes & fees

9 Nov - 10 Nov

20. Tiny Home Tranquil Oasis

Bear

Erin C.

includes taxes & fees

11 Oct - 12 Oct

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Top Massey Hotel Reviews

Holiday Inn Express & Suites Middletown by IHG

10/10 Excellent

"The group that stayed that weekend were impolite and left trash all over breakfast area. In the future maybe that group should be given a slotted time for breakfast. They were also rude to your staff and my wife. Coffee machine good but more needed. Always like when coffee/tea/water away from breakfast area. Oh, group also loud in hallways, maybe signs saying quiet area."

Sleep Inn & Suites Dover University Area

8/10 Good

"I booked two rooms. Upon arrival I was pleased to find them to be adjoining rooms. However we couldn’t use the adjoining doors as one was very hard to unlock. Once we got it unlocked we still could not open as it seemed to have been stuck. We never called staff or maintenance to fix. We had two grown sons in the adjoining room. We just used regular entry doors if we wanted to communicate with them."

Home2 Suites by Hilton Dover, DE

10/10 Excellent

"The hotel was very well managed and taken care of, the rooms were nice and clean and comfortable, the staff was very helpful, the breakfast was ok, and it was nice to have a microwave and be able to wash clothes. We were there for 6 days and the price could have been a little cheaper. All and all it was a great stay and I will utilize it for long term stay again. The swimming pool was Also a Plus!"

Find out more about Massey

Everything you need to know about Massey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Massey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Massey holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Massey holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Massey. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Massey holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Massey holiday rentals we have selected for you start as low as £87 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Massey rentals

At Expedia, we put the best Massey holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Massey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Massey holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Massey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find holiday rentals in Massey?

Yes, there are holiday rentals close to the most popular sights in Massey, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Massey has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Massey is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

What’s there to see and do in Massey?

Explore the area and family-friendly sights such as Frightland, or get out into nature at a spot like Betterton Beach. In the wider area, you’ll find Middletown Town Hall and Middletown Historic District.

What’s a holiday rental in Massey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Massey. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for small groups.

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Treat yourself

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Check prices for these dates

Our top choices for Massey holiday rentals

1. Guest Suite for up to 2 in a Victorian on the Chester River

2. Newly restored apartment in the heart of Chestertown

3. Historic Chesapeake City Stay

4. First Floor Studio Apartment in Historic Chestertown

5. Bohemia Manor Farm

6. Secluded Cottage in Middle of Chestertown

7. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

8. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

9. Wren Retweet- Country Estate in Center of C’Town

10. Beachcomber Suite

11. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

12. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

13. Country Get Away Studio Apartment

14. Sunset River Shack -amazing waterfront view

15. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

16. Turtle Cove Room

17. Nature's Haven Tiny Home

18. Elegant Family Stay • Quiet Neighborhood • Comfort

19. Mini Aruba RV/Glamping Tent

20. Tiny Home Tranquil Oasis

Find holiday rentals that suit your style

Top Massey Hotel Reviews

Holiday Inn Express & Suites Middletown by IHG

Bally's Dover Casino Resort

Holiday Inn Express Hotel & Suites Dover by IHG

DOVER INN

Fairfield Inn & Suites by Marriott Dover

Red Roof Inn & Suites Dover Downtown

Hampton Inn Middletown

Sleep Inn & Suites Dover University Area

Home2 Suites by Hilton Dover, DE

Find out more about Massey

Frequently asked questions

Go further with the Expedia app

Search Holiday Rentals in Massey

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Massey holiday rentals

1. Guest Suite for up to 2 in a Victorian on the Chester River

2. Newly restored apartment in the heart of Chestertown

3. Historic Chesapeake City Stay

4. First Floor Studio Apartment in Historic Chestertown

5. Bohemia Manor Farm

6. Secluded Cottage in Middle of Chestertown

7. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

8. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

9. Wren Retweet- Country Estate in Center of C’Town

10. Beachcomber Suite

11. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

12. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

13. Country Get Away Studio Apartment

14. Sunset River Shack -amazing waterfront view

15. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

16. Turtle Cove Room

17. Nature's Haven Tiny Home

18. Elegant Family Stay • Quiet Neighborhood • Comfort

19. Mini Aruba RV/Glamping Tent

20. Tiny Home Tranquil Oasis

Find holiday rentals that suit your style

Top Massey Hotel Reviews

Holiday Inn Express & Suites Middletown by IHG

Find out more about Massey

Frequently asked questions

Go further with the Expedia app