Middleboro Holiday Rentals

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Holiday Rentals in Middleboro

The Cedar Door Place

9.8 out of 10, Exceptional, (18)
"This is a great place to stay! Rural, yet conveniently close to town. "
The price is AU$283
includes taxes & fees
5 Oct - 6 Oct
The Cedar Door Place

Pet-Friendly Greenville Home w/ Private Yard

10.0 out of 10, Exceptional, (22)
"Enjoyed another great stay at this property! Clean, quiet and several thoughtful amenities."
Pet-Friendly Greenville Home w/ Private Yard

Hannah's Creek Farm Cottage

10.0 out of 10, Exceptional, (3)
"Lovely host, and beautiful location. We enjoyed the quiet away from town a lot."
The price is AU$268
includes taxes & fees
5 Oct - 6 Oct
Hannah's Creek Farm Cottage

Boho Bungalow off Main-one block from Lovely Park

9.0 out of 10, Wonderful, (12)
"We very much enjoyed our 1 night visit at the Boho Bungalow! The house was cozy and charming. Everything was clean and the property host gave clear information for our stay. We highly recommend this location."
The price is AU$277
includes taxes & fees
3 Oct - 4 Oct
Boho Bungalow off Main-one block from Lovely Park

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

9.0 out of 10, Wonderful, (12)
"The property is stunning and plenty of space for multiple people if needed! Hosts are extremely friendly and great at communicating as well!! Definitely a place you could come back to over and over again!!"
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

Quaker Hill Cottage on gated estate with fire pit & hiking trails

9.8 out of 10, Exceptional, (25)
"Very unique quaint cottage hidden from the city. Loved the forested area around it with the patio to the side. We saw"
The price is AU$344
includes taxes & fees
4 Oct - 5 Oct
Quaker Hill Cottage on gated estate with fire pit & hiking trails

Pet-friendly Greenville Home w/ Private Yard

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

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

2.0 star property
8.8 out of 10, Excellent, (6)
"Didn’t get in the house"
The price is AU$374
includes taxes & fees
6 Oct - 7 Oct
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

Charming Home! Prime Location! Dog-Friendly!

9.8 out of 10, Exceptional, (10)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
The price is AU$508
includes taxes & fees
29 Sept - 30 Sept
Charming Home! Prime Location! Dog-Friendly!

Leader Loft, Cozy and Quaint

10.0 out of 10, Exceptional, (4)
"Very nice loft in a neat little town along old US 40, stayed overnight while doing the 127 yard sales."
The price is AU$212
includes taxes & fees
28 Sept - 29 Sept
Leader Loft, Cozy and Quaint

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

10.0 out of 10, Exceptional, (11)
"Very clean and great amenities. Will be booking there again in the future."
The price is AU$253
includes taxes & fees
6 Oct - 7 Oct
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

Westcott Mansion with Pickleball Court & Huge Gazebo

9.8 out of 10, Exceptional, (34)
"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 AU$512
includes taxes & fees
4 Oct - 5 Oct
Westcott Mansion with Pickleball Court & Huge Gazebo

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 AU$215
includes taxes & fees
30 Sept - 1 Oct
New Hagerstown Apartment - Self Check-in. Sleeps 4+

Charming 3-bedroom house with AC, WiFi in Greenville

8.8 out of 10, Excellent, (5)
The price is AU$382
includes taxes & fees
28 Sept - 29 Sept
Charming 3-bedroom house with AC, WiFi in Greenville

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

Cumberland House - A Cozy Historical Stay

2.0 star property
Cumberland House - A Cozy Historical Stay

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 AU$794
includes taxes & fees
28 Oct - 29 Oct
Spacious House with Large yard and King-size bed

Charming 2-bedroom cabin in Lewisburg with privacy, WiFi, AC

9.8 out of 10, Exceptional, (10)
"Great spot in a nice area. Host was great! Look forward to coming back again someday! "
Charming 2-bedroom cabin in Lewisburg with privacy, WiFi, AC

Exquisite Hagerstown Home With Deck & Gazebo!

3.0 star property
Exquisite Hagerstown Home With Deck & Gazebo!

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

10.0 out of 10, Exceptional, (39)
"Very nice, clean, quiet neighborhood. Excellent place to stay."
Recently remodeled Colonial-style home with room for the whole family!
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, 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 favourite 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 depend 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 AU$212 per night. Entering your travel dates in the search wizard might find you 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?

Pet-Friendly Greenville Home w/ Private Yard: This holiday home rental outside of Middleboro is equipped with a selection of games, air conditioning and laundry facilities to help you feel comfortable during your stay. 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.