Middleboro Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Middleboro

Apartment in Lewisburg

9.6 out of 10, Exceptional, (20)
"2nd time staying. Will stay again. Very spacious and large kitchen. "
United States
Scott R.
The price is NZ$329
includes taxes & fees
23 Nov - 24 Nov
The Cedar Door Place

Cottage in Richmond

9.6 out of 10, Exceptional, (28)
"Quaint cottage in Richmond, Indiana. Very peaceful location even though close to downtown. My sisters, our daughters, and I enjoyed spending time in such a beautiful setting."
United States
Judi C.
The price is NZ$479
includes taxes & fees
25 Nov - 26 Nov
Quaker Hill Cottage on gated estate with fire pit & hiking trails

Holiday Home in Greenville

10.0 out of 10, Exceptional, (24)
"Enjoyed another great stay at this property! Clean, quiet and several thoughtful amenities."
United States
Vernon
Pet-Friendly Greenville Home w/ Private Yard

Cottage in 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 NZ$311
includes taxes & fees
30 Nov - 1 Dec
Hannah's Creek Farm Cottage

Apartment in Richmond

9.4 out of 10, Exceptional, (36)
"Property is so unique and cozy. We really enjoyed the stay. So much better than a hotel. Location is great. Walkable to many restaurants. Would definitely recommend. "
United States
Renee M.
THE STARR LOFT- Earlham, IUEast, Historic District

Holiday Home in Richmond

10.0 out of 10, Exceptional, (40)
"Great place. Highly recommend!"
United States
Jon M.
Recently remodeled Colonial-style home with room for the whole family!

Holiday Home in 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 NZ$590
includes taxes & fees
22 Nov - 23 Nov
Charming Home! Prime Location! Dog-Friendly!

Holiday Home in Richmond

9.0 out of 10, Wonderful, (12)
"Lovely house, easy check-in, great location."
United States
Heather S.
The price is NZ$321
includes taxes & fees
23 Nov - 24 Nov
Boho Bungalow off Main-one block from Lovely Park

Cabin in New Paris

10.0 out of 10, Exceptional, (2)
"The tiny house was just as described and very comfortable. My favorite part was the huge lakefront lot with beautiful views and lots of privacy."
United States
Larry
Tiny Home at Camp Mahanaim - New Paris, OH - Private Lake

Holiday Home in Richmond

9.8 out of 10, Exceptional, (34)
"We had the best time. House was gorgeous and unique. Perfect place for our group as everyone had their own room and their own bed! Would absolutely stay here again. "
United States
Megan H.
The price is NZ$595
includes taxes & fees
25 Nov - 26 Nov
Westcott Mansion with Pickleball Court & Huge Gazebo

Apartment in Hagerstown

10.0 out of 10, Exceptional, (11)
"Very clean and great amenities. Will be booking there again in the future."
United States
Lisa B.
The price is NZ$293
includes taxes & fees
1 Dec - 2 Dec
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

Holiday Home in Greens Fork

8.8 out of 10, Excellent, (15)
"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!!"
United States
Madison M.
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

Holiday Home in Wayne Township

10.0 out of 10, Exceptional, (9)
"Great setting for 6 old guys to sit around and reminisce. Beautiful property and the summer kitchen is great."
United Kingdom
Mark R.
18 Acre Farm - Pickleball, Pond, Outdoor Kitchen

Holiday Home in Greenville

9.0 out of 10, Wonderful, (8)
"Nice place good location. Would highly recommend to anyone."
United States
Steven M.
The price is NZ$444
includes taxes & fees
23 Nov - 24 Nov
Charming 3-bedroom house with AC, WiFi in Greenville

Apartment in Hagerstown

9.2 out of 10, Wonderful, (20)
"Great little apartment. Just what we needed for overnight. "
United States
Kim M.
The price is NZ$247
includes taxes & fees
3 Dec - 4 Dec
New Hagerstown Apartment - Self Check-in. Sleeps 4+

Cabin in 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

Holiday Home in Greenville

2.0 star property
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 NZ$440
includes taxes & fees
24 Nov - 25 Nov
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

Cottage in Greenville

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

Holiday Home in West Alexandria

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. "
United States
Deidre S.
The price is NZ$918
includes taxes & fees
23 Nov - 24 Nov
Spacious House with Large yard and King-size bed

Holiday Home in Lewisburg

2.0 star property
Cumberland House - A Cozy Historical Stay
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.

Black Friday Sale

Save up to 40% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

Top Middleboro Hotel Reviews

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 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 NZ$247 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?

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.