Holiday Rentals in Middleboro

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Holiday Rentals in Middleboro

Our top choices for Middleboro holiday rentals

Pet-Friendly Greenville Home w/ Private Yard

10.0 out of 10, Exceptional, (21)
"Enjoyed another great stay at this property! Clean, quiet and several thoughtful amenities."
Pet-Friendly Greenville Home w/ Private Yard

Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

9.0 out of 10, Wonderful, (10)
"Nice, quiet, peaceful."
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

The Cedar Door Place

10.0 out of 10, Exceptional, (15)
"This is a great place to stay! Rural, yet conveniently close to town. "
The price is €160
includes taxes & fees
7 Sept - 8 Sept
The Cedar Door Place

Charming 3-bedroom house with AC, WiFi in Greenville

8.0 out of 10, Very good, (3)
"Nice place good location. Would highly recommend to anyone."
The price is €219
includes taxes & fees
29 Aug - 30 Aug
Charming 3-bedroom house with AC, WiFi in Greenville

New Hagerstown Apartment - Self Check-in. Sleeps 4+

9.2 out of 10, Wonderful, (20)
"Always a pleasure and the location is perfect for seeing family!"
The price is €123
includes taxes & fees
10 Sept - 11 Sept
New Hagerstown Apartment - Self Check-in. Sleeps 4+

Hannah's Creek Farm Cottage

10.0 out of 10, Exceptional, (2)
"The location was easy to find using Google maps. Sharon was lovely. She met me when I arrived. She helped me carry in my many bags. She showed me where everything was and how to use it. The loft is probably great for someone in good shape but I knew that going in. It was just me and my dog so we slept on the pull out couch. I assumed correctly the water was from a well so I brought some bottled water to drink. It is drinkable but has a well water taste. The cottage is heated through geo-thermal...
The price is €153
includes taxes & fees
26 Sept - 27 Sept
Hannah's Creek Farm Cottage

Charming Home! Prime Location! Dog-Friendly!

9.8 out of 10, Exceptional, (9)
"We are from Richmond originally and come back to visit family often. Definitely will be back. Great stay, great host, very accommodating, and clean. Highly recommend if you are in the area. "
The price is €289
includes taxes & fees
1 Sept - 2 Sept
Charming Home! Prime Location! Dog-Friendly!

Newly renovated studio in Hagerstown--Self Check-in

9.6 out of 10, Exceptional, (26)
"Loved the property close to whatever you need for seeing local attractions or family/friends."
The price is €117
includes taxes & fees
10 Sept - 11 Sept
Newly renovated studio in Hagerstown--Self Check-in

The Rivertown Lodge near Brookville Lake, Quakertown Marina and Whitewater SP

10.0 out of 10, Exceptional, (16)
"Great for a big group"
The Rivertown Lodge near Brookville Lake, Quakertown Marina and Whitewater SP

Recently remodeled Colonial-style home with room for the whole family!

10.0 out of 10, Exceptional, (38)
"A very comfortable home for a family stay. The kitchen is well equipped for a family stay. Backyard fire pit is a plus for S’mores. Very quiet neighborhood. "
Recently remodeled Colonial-style home with room for the whole family!

Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

2.0 star property
7.4 out of 10, Good, (3)
"This is a beautiful home with exceptional amenities. Is just about the closest home to the fairgrounds. Does need a gas grill.Thank you for letting us stay!!"
The price is €217
includes taxes & fees
1 Sept - 2 Sept
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

9.8 out of 10, Exceptional, (9)
"Very clean and great amenities. Will be booking there again in the future."
The price is €145
includes taxes & fees
3 Sept - 4 Sept
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

Boho Bungalow off Main-one block from Lovely Park

8.8 out of 10, Excellent, (10)
"Neighborhood a little blighted. Little house is a great piece of history. Very well maintained, appointed and loved. We were comfortable."
The price is €158
includes taxes & fees
28 Sept - 29 Sept
Boho Bungalow off Main-one block from Lovely Park

Pet-friendly Greenville Home w/ Private Yard

3.0 star property
Pet-friendly Greenville Home w/ Private Yard

THE STARR LOFT- Earlham, IUEast, Historic District

9.4 out of 10, Exceptional, (32)
"I wasn't expecting that a visit to my small hometown would end up being the nicest vacation stay I've had but it was. Walking distance to some fun restaurants and a great record store. Property itself was beautiful and well maintained in a renovated loft space. Lots of charm and attention to detail. This place makes me want to find reasons to visit Richmond more often!"
THE STARR LOFT- Earlham, IUEast, Historic District

The Red House

9.6 out of 10, Exceptional, (18)
"This was our 2nd stay at the red house while in town to visit family. Perfect location and space for our family of four. Friendly communication with the owner. Would happily stay again. Recommend!"
The Red House

Spacious House with Large yard and King-size bed

10.0 out of 10, Exceptional, (1)
"Amazing renovations. Tons of space. Thank you for the hospitality, we had a great time! And Thank You for the cookies! Kiddos loved them. "
The price is €442
includes taxes & fees
28 Sept - 29 Sept
Spacious House with Large yard and King-size bed

Cumberland House - A Cozy Historical Stay

2.0 star property
Cumberland House - A Cozy Historical Stay

Westcott Mansion with Pickleball Court & Huge Gazebo

9.8 out of 10, Exceptional, (33)
"We had a nice time celebrating my sons graduation from Earlham college. There was plenty of room for everyone to have their own bedroom. Very unique property with very nice furnishings. A historic property. We had everything we needed for our stay. Definitely would recommend."
The price is €292
includes taxes & fees
18 Sept - 19 Sept
Westcott Mansion with Pickleball Court & Huge Gazebo

Leader Loft, Cozy and Quaint

10.0 out of 10, Exceptional, (2)
"Very nice loft in a neat little town along old US 40, stayed overnight while doing the 127 yard sales."
The price is €135
includes taxes & fees
2 Sept - 3 Sept
Leader Loft, Cozy and Quaint
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middleboro Hotel Reviews

Find out more about Middleboro

Find out more about Middleboro

Everything you need to know about Middleboro 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 Middleboro 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 Middleboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middleboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middleboro. 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 Middleboro 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 Middleboro holiday rentals we have selected for you start as low as €117 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middleboro rentals

At Expedia, we put the best Middleboro 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 Middleboro 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 Middleboro 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 Middleboro. 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 Middleboro?

Yes, there are holiday rentals close to the most popular sights in Middleboro, 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 Middleboro has to offer?

Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.: This holiday home rental outside of Middleboro is located in the city centre, and has a balcony, a pool table and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Middleboro?

While exploring the area, visit family-friendly sights like Warm Glow Candle Company, or get outside and enjoy nature at Hayes Arboretum. In the wider area, you’ll find Indiana University East and Richmond Mall.

What are holiday rentals like in Middleboro?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middleboro. Holiday rentals feature amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a family trip.