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Middleboro Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Middleboro vacation rentals

A hotel lobby with a reception desk, a dining area with round tables and chairs, a kitchen area, and a window with a view.

1. King Bed Non-Smoking

King Bed Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (151 reviews)
"Had everything we needed for our visit,non smoking rooms kept things fresh too!"
United States
Anonymous traveler
$62 nightly
The price is $69
Aug 30 - Aug 31
Total with taxes and fees
King Bed Non-Smoking
A hotel room with two beds, a small table, a mirror, and a bathroom with a sink and toilet.

2. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (115 reviews)
"Loved how cozy and inviting this place felt!"
United States
Anonymous traveler
$67 nightly
The price is $74
Aug 30 - Aug 31
Total with taxes and fees
2 Queen Beds Non-Smoking
A modern living room with a sofa, armchair, and a white spiral staircase.

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

Quaker Hill Cottage on gated estate with fire pit & hiking trails
Richmond
9.2 out of 10, Wonderful, (35 reviews)
"Very nice place to spend the night while passing through on Route 70. The Thistlethwaite Falls are only minutes away and were a perfect evening activity after driving all day."
United States
Jon and Keri C.
$200 nightly
The price is $224
Aug 30 - Aug 31
Total with taxes and fees
Quaker Hill Cottage on gated estate with fire pit & hiking trails
A grand staircase with ornate wooden railings and a decorative balustrade, leading to a room with large stained glass windows and a chandelier.

4. Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (40 reviews)
"This is a wonderful historic property if you're into a vintage stay. We were. The home is lovely. The only disadvantages are not having a host on-site and having to get luggage up the stairs without an elevator or bellhop assitance; there are no bedrooms on the ground floor. And being vintage, it takes quite a while to adjust the temperature to where you want it. Also, it would be helpful to have television instructions; we were never able to figure out how to get anything on the TV."
United States
Debbie
$297 nightly
The price is $333
Aug 30 - Aug 31
Total with taxes and fees
Westcott Mansion with Pickleball Court & Huge Gazebo
A modern interior with leather chairs, a wooden cabinet, and large windows offering a view of greenery.

5. 18 Acre Farm - Pickleball, Pond, Outdoor Kitchen

18 Acre Farm - Pickleball, Pond, Outdoor Kitchen
Wayne Township
10.0 out of 10, Exceptional, (11 reviews)
"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.
$713 nightly
The price is $771
Aug 30 - Aug 31
Total with taxes and fees
18 Acre Farm - Pickleball, Pond, Outdoor Kitchen
A cozy room with exposed brick walls, a bed with a knitted blanket, a wooden table with chairs, and hanging wicker lamps.

6. Leader Loft, Cozy and Quaint

Leader Loft, Cozy and Quaint
Lewisburg
9.8 out of 10, Exceptional, (20 reviews)
"Great place to stay!"
United States
Jessica C.
$135 nightly
The price is $141
Aug 30 - Aug 31
Total with taxes and fees
Leader Loft, Cozy and Quaint
A two-story house with a steeply pitched roof, a yellow front door, and a number '405' on the side.

7. Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (19 reviews)
"The host was awesome and completely goes the extra mile! "
United States
Rondaq C.
$294 nightly
The price is $329
Sep 8 - Sep 9
Total with taxes and fees
Charming Home! Prime Location! Dog-Friendly!
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a microwave.

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

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.4 out of 10, Exceptional, (27 reviews)
"Great location and just what we needed for a relaxing weekend in Hagerstown."
United States
Emily E.
$131 nightly
The price is $146
Sep 1 - Sep 2
Total with taxes and fees
New Hagerstown Apartment - Self Check-in. Sleeps 4+
A modern kitchen with stainless steel appliances, wooden cabinets, and a white tiled backsplash.

9. 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, (17 reviews)
"We had a great time and this place has everything that you need!"
United States
kirk h.
$146 nightly
The price is $164
Aug 31 - Sep 1
Total with taxes and fees
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
A living room with a beige sofa, a grey recliner, a flat-screen TV on a wooden stand, and a window with curtains.

10. Comfortable Modern Stay Quiet 1BR Retreat Near Dayton, Eaton, Miami U& Richmond

Comfortable Modern Stay Quiet 1BR Retreat Near Dayton, Eaton, Miami U& Richmond
Eaton
10.0 out of 10, Exceptional, (5 reviews)
"30 minutes from Miami U on graduation weekend was a great find. "
United States
Virginia
$138 nightly
The price is $138
Sep 14 - Sep 15
Total with taxes and fees
Comfortable Modern Stay Quiet 1BR Retreat Near Dayton, Eaton, Miami U& Richmond
A dining area with a large wooden table set for six, surrounded by wooden chairs. A chandelier hangs above the table, and the room features white cabinetry and a patterned rug.

11. 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, (5 reviews)
"The house was spacious, beautiful, and very clean. It was perfectly located for our needs. We highly recommend this house. Marci was a wonderful host!"
United States
Susan W.
$525 nightly
The price is $550
Aug 30 - Aug 31
Total with taxes and fees
Spacious House with Large yard and King-size bed
A rustic kitchen with wooden beams, a sink, a refrigerator, and a window with curtains.

12. Hannah's Creek Farm Cottage

Hannah's Creek Farm Cottage
Liberty
9.8 out of 10, Exceptional, (8 reviews)
"Lovely host, and beautiful location. We enjoyed the quiet away from town a lot."
United States
Melissa H.
$155 nightly
The price is $174
Aug 30 - Aug 31
Total with taxes and fees
Hannah's Creek Farm Cottage
A living room with a brown sofa, a brown armchair, a coffee table with a tray, a lamp, and a door with a view of the outside.

13. Gigi's Place - Historic Charm. Modern Comfort.

Gigi's Place - Historic Charm. Modern Comfort.
Eaton
10.0 out of 10, Exceptional, (3 reviews)
"Everything was just perfect! It’s an easy drive to Miami University of Ohio for anyone visiting campus. Lindsay is a terrific host and communicated so well with me. She is very hospitable and provided a charming place to stay - super clean, comfortable & cozy!"
United States
Karen M.
$142 nightly
The price is $151
Aug 31 - Sep 1
Total with taxes and fees
Gigi's Place - Historic Charm. Modern Comfort.
A rustic wooden interior with a stone fireplace, wooden beams, a long dining table with chairs, and hanging lanterns.

14. Governor's Cabin in Arcanum, Ohio

Governor's Cabin in Arcanum, Ohio
Arcanum
$444 nightly
The price is $444
Aug 30 - Aug 31
Total with taxes and fees
Governor's Cabin in Arcanum, Ohio

15. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
$292 nightly
The price is $326
Aug 30 - Aug 31
Total with taxes and fees
Pets Welcome! Quiet Economy Home w/ Spacious Yard

16. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
2.0 out of 10, (1 review)
"Bed bugs in upstairs bedroom!!!Unfortunately we had a terrible experience both during and following our stay. During the stay the air conditioning was not functioning properly and we were forced to use portable AC units that didn’t get the temperature below 78 in the house.Three people sleeping upstairs had bed bug bites and upon searching the two beds we found numerous bugs. We promptly made the property owner aware of the situation and requested our stay be refunded due to the inconvenience...
United States
Payton L.
$300 nightly
The price is $336
Aug 30 - Aug 31
Total with taxes and fees
Pets Welcome! Quiet Economy Home w/ Spacious Yard
A couple embracing on wooden steps with a rustic backdrop.

17. 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.
$320 nightly
The price is $320
Aug 31 - Sep 1
Total with taxes and fees
WAGON 1 in The Graystone Ranch in the Woods
A couple embracing on wooden steps with a rustic backdrop.

18. 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.
$409 nightly
The price is $409
Aug 31 - Sep 1
Total with taxes and fees
WAGON 2 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

Motel 6 Richmond, IN

Motel 6 Richmond, IN

8/10 Good
"It was clean motel and ok for night stay. First room we got had some smoke smell and they changed room immediately which was good smooth check in and check out. Lot of places to eat nearby."
Rajeshwara 1-night trip
Posted 2 hours ago
Motel 6 Richmond, IN

Find out more about Middleboro

Everything you need to know about Middleboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middleboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middleboro vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middleboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $69 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middleboro rentals

At Expedia, we put the best Middleboro vacation 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 vacation.

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 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?

Charming Home! Prime Location! Dog-Friendly!: You might want to consider this vacation home rental near Middleboro, which offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. 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. You can relax into your vacation with a garden and a selection of games.

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 Richmond Mall and Richmond Art Museum.

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.