Middleboro Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Middleboro

Our top choices for Middleboro vacation rentals

The Cedar Door Place
Outdoor dining

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 ￥15,323
￥26,912 total
includes taxes & fees
Sep 8 - Sep 9
The Cedar Door Place
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
Living area

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

9.0 out of 10, Wonderful, (11)
"Nice, quiet, peaceful."
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
Hannah's Creek Farm Cottage
Private kitchen

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 ￥18,506
￥25,701 total
includes taxes & fees
Sep 8 - Sep 9
Hannah's Creek Farm Cottage
Boho Bungalow off Main-one block from Lovely Park
Interior

Boho Bungalow off Main-one block from Lovely Park

9.0 out of 10, Wonderful, (11)
"Neighborhood a little blighted. Little house is a great piece of history. Very well maintained, appointed and loved. We were comfortable."
The price is ￥14,065
￥26,531 total
includes taxes & fees
Sep 7 - Sep 8
Boho Bungalow off Main-one block from Lovely Park
Pet-Friendly Greenville Home w/ Private Yard
Fridge, microwave, stovetop, dishwasher

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
Charming Home! Prime Location! Dog-Friendly!
Terrace/patio

Charming Home! Prime Location! Dog-Friendly!

9.8 out of 10, Exceptional, (10)
"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 ￥23,384
￥48,807 total
includes taxes & fees
Sep 14 - Sep 15
Charming Home! Prime Location! Dog-Friendly!
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Smart TV, fireplace

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 ￥8,661
￥20,480 total
includes taxes & fees
Sep 8 - Sep 9
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Charming 3-bedroom house with AC, WiFi in Greenville
Property grounds

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 ￥23,244
￥36,717 total
includes taxes & fees
Sep 8 - Sep 9
Charming 3-bedroom house with AC, WiFi in Greenville
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (10)
"Very clean and great amenities. Will be booking there again in the future."
The price is ￥10,526
￥24,227 total
includes taxes & fees
Sep 8 - Sep 9
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
Exterior

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 ￥22,918
￥36,391 total
includes taxes & fees
Sep 8 - Sep 9
Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.
The Rivertown Lodge near Brookville Lake, Quakertown Marina and Whitewater SP
Interior

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
House, 2 Bedrooms, Microwave | Living room

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
Private kitchen

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 ￥48,708
￥75,954 total
includes taxes & fees
Sep 8 - Sep 9
Spacious House with Large yard and King-size bed
THE STARR LOFT- Earlham, IUEast, Historic District
Interior

THE STARR LOFT- Earlham, IUEast, Historic District

9.4 out of 10, Exceptional, (32)
"Spacious, Unique property. Incredible location within the Starr Historic Distric of Richmond.Enjoyed the weekend exploring and 5 minutes from the Earlham College Campus."
THE STARR LOFT- Earlham, IUEast, Historic District
Pet-friendly Greenville Home w/ Private Yard
House (3 Bedrooms) | Interior

Pet-friendly Greenville Home w/ Private Yard

3.0 star property
Pet-friendly Greenville Home w/ Private Yard
The Red House
Property grounds

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

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

9.8 out of 10, Exceptional, (9)
"Great spot in a nice area. Host was great! Look forward to coming back again someday! "
The price is ￥29,314
￥32,867 total
includes taxes & fees
Sep 9 - Sep 10
Charming 2-bedroom cabin in Lewisburg with privacy, WiFi, AC
Westcott Mansion with Pickleball Court & Huge Gazebo
8 bedrooms, WiFi, bed sheets

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 ￥24,428
￥49,081 total
includes taxes & fees
Sep 6 - Sep 7
Westcott Mansion with Pickleball Court & Huge Gazebo
Recently remodeled Colonial-style home with room for the whole family!
Exterior

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

10.0 out of 10, Exceptional, (39)
"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!
Leader Loft, Cozy and Quaint
1 bedroom, WiFi, bed sheets

Leader Loft, Cozy and Quaint

10.0 out of 10, Exceptional, (3)
"Very nice loft in a neat little town along old US 40, stayed overnight while doing the 127 yard sales."
The price is ￥14,253
￥22,710 total
includes taxes & fees
Sep 15 - Sep 16
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

Search for holiday rentals in Middleboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Middleboro using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middleboro!

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?

Pet-Friendly Greenville Home w/ Private Yard: Visitors like this Middleboro vacation home rental. It 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 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 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.