Middleboro Holiday Rentals

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Holiday Rentals in Middleboro

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

Richmond
9.8 out of 10, Exceptional, (25)
"Such an interesting place. It was a great stay. We would definitely stay there again!"
United States
Marisa H.
The price is AU$343
includes taxes & fees
21 Nov - 22 Nov
Quaker Hill Cottage on gated estate with fire pit & hiking trails

The Cedar Door Place

Lewisburg
9.8 out of 10, Exceptional, (18)
"This is a great place to stay! Rural, yet conveniently close to town. "
United States
John S.
The price is AU$285
includes taxes & fees
16 Nov - 17 Nov
The Cedar Door Place

Pet-Friendly Greenville Home w/ Private Yard

Greenville
10.0 out of 10, Exceptional, (24)
"Another terrific stay! Its like a home away from home and very accommodating with the fenced in backyard and provided dog bags."
United States
Abraham S.
Pet-Friendly Greenville Home w/ Private Yard

Boho Bungalow off Main-one block from Lovely Park

Richmond
9.0 out of 10, Wonderful, (12)
"My husband, son, and I stayed here the weekend of our daughter’s graduation from Miami University. It was so cute and easy to access. The communication was awesome and check in/check out process was simple. Would definitely recommend."
United States
Kelly R.
The price is AU$277
includes taxes & fees
14 Nov - 15 Nov
Boho Bungalow off Main-one block from Lovely Park

Charming Home! Prime Location! Dog-Friendly!

Richmond
10.0 out of 10, Exceptional, (12)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
The price is AU$510
includes taxes & fees
14 Nov - 15 Nov
Charming Home! Prime Location! Dog-Friendly!

Hannah's Creek Farm Cottage

Liberty
9.6 out of 10, Exceptional, (5)
"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...
United States
Saundra R.
The price is AU$269
includes taxes & fees
16 Nov - 17 Nov
Hannah's Creek Farm Cottage

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

Greens Fork
9.0 out of 10, Wonderful, (13)
"The atmosphere and views are stunning. The home is spacious for families. We enjoyed our stay. "
United States
Donna H.
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

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

Hagerstown
10.0 out of 10, Exceptional, (11)
"Lovely property in Hagerstown. We stayed here with my 82 year old father while visiting family. Perfect accommodations! Very clean & comfortable. We had a little hiccup with our code to check in, but once Michelle saw our note, we got it fixed right away. Convenient to Main Street shops & food. We would definitely stay here again on our next trip!"
United States
Laura T.
The price is AU$253
includes taxes & fees
17 Nov - 18 Nov
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

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

Richmond
10.0 out of 10, Exceptional, (40)
"Very nice, clean, quiet neighborhood. Excellent place to stay."
United States
Matt H.
Recently remodeled Colonial-style home with room for the whole family!

Tiny Home at Camp Mahanaim - New Paris, OH - Private Lake

New Paris
10.0 out of 10, Exceptional, (2)
"Very peaceful and safe. Comfortable and well supplied."
United States
Laura B.
Tiny Home at Camp Mahanaim - New Paris, OH - Private Lake

Westcott Mansion with Pickleball Court & Huge Gazebo

Richmond
9.8 out of 10, Exceptional, (34)
"The house was beautiful and so interesting! The owners were very responsive to our questions. We really enjoyed our stay!"
United States
Jeff N.
The price is AU$515
includes taxes & fees
20 Nov - 21 Nov
Westcott Mansion with Pickleball Court & Huge Gazebo

18 Acre Farm - Pickleball, Pond, Outdoor Kitchen

Wayne Township
10.0 out of 10, Exceptional, (9)
"Super week stay a very unique well equipped house - From the inside kitchen to the outdoor kitchen and grilling area plus wildlife galore, nothing is better then eating breakfast and deers show up and pose outside the windows The house is fitted in a retro style with modern amenities. Would definitely stay there again"
United States
Robin A.
18 Acre Farm - Pickleball, Pond, Outdoor Kitchen

Cumberland House - A Cozy Historical Stay

2.0 star property
Lewisburg
Cumberland House - A Cozy Historical Stay

Charming 3-bedroom house with AC, WiFi in Greenville

Greenville
9.0 out of 10, Wonderful, (8)
"Nice place good location. Would highly recommend to anyone."
United States
Steven M.
The price is AU$384
includes taxes & fees
23 Nov - 24 Nov
Charming 3-bedroom house with AC, WiFi in Greenville

Exquisite Hagerstown Home With Deck & Gazebo!

3.0 star property
Hagerstown
Exquisite Hagerstown Home With Deck & Gazebo!

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

Hagerstown
9.2 out of 10, Wonderful, (20)
"The apartment was excellent and everything about the process was 5-stars. We will definitely stay here again next time we are in town!"
United States
Cole T.
The price is AU$218
includes taxes & fees
24 Nov - 25 Nov
New Hagerstown Apartment - Self Check-in. Sleeps 4+

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

Lewisburg
10.0 out of 10, Exceptional, (13)
"My stay was very enjoyable. The cabin is located in a quiet rural setting with a pleasant forest path out the back yard and a field in front. The cabin is equipped with modern appliances and cookware that support meal preparation, so visitors can be self sufficient if they desire to enjoy the quiet setting. It can comfortably sleep a couple and two children or 4 adults if two of them don’t mind sleeping in bunk beds. This a great place for a quiet stay, and one can even entertain guests for...
United States
Daniel
Charming 2-bedroom cabin in Lewisburg with privacy, WiFi, AC

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

Brownsville
10.0 out of 10, Exceptional, (18)
"I was blown away by how beautiful and clean the property was. Extremely modern and new, spacious and comfortable! If you are spending the weekend at Brookville lake I highly recommend staying here. It’s a quick drive to the lake and a wonderful place to relax afterwards!"
United States
Brian E.
The Rivertown Lodge near Brookville Lake, Quakertown Marina and Whitewater SP

Cozy Cabin with fireplace, hot tub & hiking trails

Richmond
8.4 out of 10, Very good, (5)
"The cabin is an absolute dream! It feels like a cozy cottage nestled in the woods, yet you’re just moments away from shops and restaurants. I can’t express enough how incredible our stay was! As a mom of two busy little boys, finding time to relax can be challenging, but this place offers such privacy and a delightful heated pool that it felt like my own personal retreat. The grounds are stunning, and you’re just a short stroll away from a breathtaking waterfall. I wholeheartedly recommend this...
United States
T B.
Cozy Cabin with fireplace, hot tub & hiking trails

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

2.0 star property
Greenville
9.0 out of 10, Wonderful, (8)
"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!!"
United States
Tonia E.
The price is AU$381
includes taxes & fees
24 Nov - 25 Nov
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
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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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$218 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.