Middleboro Vacation Rentals

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Our top choices for Middleboro vacation rentals

Leader Loft, Cozy and Quaint

Leader Loft, Cozy and Quaint
Lewisburg
10.0 out of 10, Exceptional, (8 reviews)
"We enjoyed our visit here very much. The unit is well appointed and the bed is extremely comfortable. Lots of cute little shops to visit within walking distance. "
United States
Amanda
The price is CA $110
CA $187 total
includes taxes & fees
Feb 19 - Feb 20
Leader Loft, Cozy and Quaint

The Cedar Door Place

The Cedar Door Place
Lewisburg
9.8 out of 10, Exceptional, (28 reviews)
"Host was easy to work with and we appreciated her kindness. Home was clean and exactly how it was pictured. We had a great stay. "
United States
Sarah M.
The price is CA $141
CA $248 total
includes taxes & fees
Feb 19 - Feb 20
The Cedar Door Place

Eaton OH 1-queen bed condo, full kitchen near Richmond In and Oxford sleeps two

Eaton OH 1-queen bed condo, full kitchen near Richmond In and Oxford sleeps two
Eaton
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly, house was set up for everything we needed. If i could give them more then 5 stars i would. We absolutely loved this place!"
United States
Mylee J.
The price is CA $98
CA $132 total
includes taxes & fees
Feb 23 - Feb 24
Eaton OH 1-queen bed condo, full kitchen near Richmond In and Oxford sleeps two

Hannah's Creek Farm Cottage

Hannah's Creek Farm Cottage
Liberty
9.6 out of 10, Exceptional, (5 reviews)
"Lovely host, and beautiful location. We enjoyed the quiet away from town a lot."
United States
Melissa H.
The price is CA $170
CA $237 total
includes taxes & fees
Feb 22 - Feb 23
Hannah's Creek Farm Cottage

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

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.2 out of 10, Wonderful, (21 reviews)
"Great little apartment. Just what we needed for overnight. "
United States
Kim M.
The price is CA $80
CA $189 total
includes taxes & fees
Feb 24 - Feb 25
New Hagerstown Apartment - Self Check-in. Sleeps 4+

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

Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
Greenville
9.2 out of 10, Wonderful, (11 reviews)
"House was perfect for our family to stay for our daughter's wedding "
United States
Molly L.
The price is CA $211
CA $334 total
includes taxes & fees
Feb 23 - Feb 24
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+

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Hagerstown
10.0 out of 10, Exceptional, (12 reviews)
"Very conveniently located with clear instructions about amenities. We will stay here again sometime."
United States
MaryandMichael P.
The price is CA $108
CA $235 total
includes taxes & fees
Mar 10 - Mar 11
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park
Richmond
9.2 out of 10, Wonderful, (15 reviews)
"Lovely house, easy check-in, great location."
United States
Heather S.
The price is CA $130
CA $244 total
includes taxes & fees
Mar 4 - Mar 5
Boho Bungalow off Main-one block from Lovely Park

Charming 3-bedroom house with AC, WiFi in Greenville

Charming 3-bedroom house with AC, WiFi in Greenville
Greenville
9.2 out of 10, Wonderful, (9 reviews)
"Nice place good location. Would highly recommend to anyone."
United States
Steven M.
The price is CA $214
CA $337 total
includes taxes & fees
Feb 20 - Feb 21
Charming 3-bedroom house with AC, WiFi in Greenville

Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (35 reviews)
"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 CA $225
CA $452 total
includes taxes & fees
Feb 20 - Feb 21
Westcott Mansion with Pickleball Court & Huge Gazebo

Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (13 reviews)
"Great house! Just what we needed and in an amazing Richmond neighborhood. "
United States
Jason S.
The price is CA $215
CA $448 total
includes taxes & fees
Feb 19 - Feb 20
Charming Home! Prime Location! Dog-Friendly!

Spacious House with Large yard and King-size bed

Spacious House with Large yard and King-size bed
West Alexandria
10.0 out of 10, Exceptional, (2 reviews)
"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 CA $449
CA $693 total
includes taxes & fees
Feb 19 - Feb 20
Spacious House with Large yard and King-size bed

WAGON 2 in The Graystone Ranch in the Woods

WAGON 2 in The Graystone Ranch in the Woods
Arcanum
10.0 out of 10, Exceptional, (1 review)
"My patents were celebrating their 64 year anniversary. We wanted to celebrate with a short trip and this was the perfect location. The property was beautiful and we enjoyed the walk in the woods and fishing. The covered wagon was a unique stay and one we will remember."
United States
Dawn B.
The price is CA $341
CA $554 total
includes taxes & fees
Mar 5 - Mar 6
WAGON 2 in The Graystone Ranch in the Woods

WAGON 1 in The Graystone Ranch in the Woods

WAGON 1 in The Graystone Ranch in the Woods
Arcanum
10.0 out of 10, Exceptional, (1 review)
"My wife and I stayed in one of the wagons located in Arcanum. It was a great stay. Peaceful, quiet, and just a great experience! We would stay again."
United States
Brent C.
The price is CA $341
CA $554 total
includes taxes & fees
Mar 5 - Mar 6
WAGON 1 in The Graystone Ranch in the Woods
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middleboro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Middleboro?

Yes, we have vacation rentals close to the most popular sights in Middleboro, or you can choose a more secluded option if you're looking for relaxation.

What's the top vacation rental in Middleboro?

Westcott Mansion with Pickleball Court & Huge Gazebo: Visitors like this Middleboro vacation home rental. It offers a fireplace, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Middleboro?

While exploring the area, visit family-friendly sights like Glenn Miller Park, or get outside and enjoy nature at Hayes Arboretum. In the larger area, you’ll find Indiana University East and Richmond Mall.

What are vacation rentals like in Middleboro?

Vacation rentals are privately owned properties you can reserve for several days or longer in Middleboro. Vacation rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for families.