Best Vacation Homes in Middleborough
Cottage
10.0(45 Reviews)
2 Bedrooms
1 Bath
4 Guests
850 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
AU $804/Night
7 Nights - AU $5,627
House
10.0(4 Reviews)
3 Bedrooms
6 Baths
6 Guests
172.22 ft²
- Parking
- Balcony/Terrace
View- Kitchen
AU $205/Night
7 Nights - AU $1,434
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
Ocean View- View
- Kitchen
- Air Conditioner
AU $951/Night
7 Nights - AU $6,655
Apartment
10.0(43 Reviews)
2 Bedrooms
1 Bath
4 Guests
650 ft²
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
AU $338/Night
7 Nights - AU $2,370
Apartment
10.0(3 Reviews)
1 Bedroom
2 Baths
2 Guests
796.53 ft²
- Parking
Internet
Child Friendly
Security/Safety
AU $279/Night
7 Nights - AU $1,953
Cottage
10.0(21 Reviews)
3 Bedrooms
1 Bath
8 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $499/Night
7 Nights - AU $3,496
Apartment
10.0(20 Reviews)
2 Bedrooms
2 Baths
8 Guests
1615 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $867/Night
7 Nights - AU $6,071
Cottage
10.0(18 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
AU $341/Night
7 Nights - AU $2,390
Middleborough Luxury Rentals
New
House
3 Bedrooms
2 Baths
8 Guests
Private Pool- Parking
Pool- Balcony/Terrace
AU $3,000/Night
7 Nights - AU $21,002
Hotel
9.7(17 Reviews)
7 Baths
282.94 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
AU $2,452/Night
7 Nights - AU $17,166
House
6 Bedrooms
4 Baths
15 Guests
3993 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $2,440/Night
7 Nights - AU $17,080
House
10.0(9 Reviews)
7 Bedrooms
7 Baths
25 Guests
9300 ft²
- Oceanfront
Hot Tub- Parking
- Ocean View
AU $2,437/Night
7 Nights - AU $17,062
New
Cottage
5 Bedrooms
3 Baths
12 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
AU $1,777/Night
7 Nights - AU $12,439
House
9.8(14 Reviews)
3 Bedrooms
1 Bath
10 Guests
1798 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
AU $1,744/Night
7 Nights - AU $12,211
House
3 Bedrooms
1 Bath
6 Guests
- Air Conditioner
- Internet
- Security/Safety
AU $1,734/Night
7 Nights - AU $12,136
House
10.0(3 Reviews)
6 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
AU $1,555/Night
7 Nights - AU $10,887
Middleborough Pet Friendly Vacation Rentals
Apartment
10.0(10 Reviews)
3 Bedrooms
2 Baths
8 Guests
1722 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $906/Night
7 Nights - AU $6,346
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
AU $302/Night
7 Nights - AU $2,113
Apartment
1 Bedroom
1 Bath
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
AU $364/Night
7 Nights - AU $2,546
Apartment
10.0(7 Reviews)
2 Bedrooms
2 Baths
9 Guests
1722 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $914/Night
7 Nights - AU $6,401
Apartment
9.5(4 Reviews)
1 Bedroom
1 Bath
6 Guests
452.08 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
AU $232/Night
7 Nights - AU $1,627
House
10.0(7 Reviews)
2 Bedrooms
1 Bath
6 Guests
1025 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $592/Night
7 Nights - AU $4,147
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
3993 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $775/Night
7 Nights - AU $5,423
Apartment
10.0(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
1722 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $914/Night
7 Nights - AU $6,401
Middleborough Large Vacation Homes
House
10.0(24 Reviews)
4 Bedrooms
3 Baths
10 Guests
3047 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
AU $1,064/Night
7 Nights - AU $7,449
House
10.0(1 Review)
1 Bedroom
4 Baths
12 Guests
- Parking
- Child Friendly
Barbecue/Outdoor Cooking
AU $1,015/Night
7 Nights - AU $7,104
House
Expansive Cape Cod Retreat in Wareham: Modern Amenities and Traditional Charm with Private Courtyard
10.0(13 Reviews)
3 Bedrooms
1 Bath
12 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $990/Night
7 Nights - AU $6,926
Bed & Breakfast
9.9(96 Reviews)
3 Bedrooms
3 Baths
12 Guests
516.67 ft²
Private Beach- Oceanfront
- Parking
- Ocean View
AU $355/Night
7 Nights - AU $2,485
House
10.0(10 Reviews)
5 Bedrooms
3 Baths
12 Guests
2800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $1,471/Night
7 Nights - AU $10,298
House
10.0(2 Reviews)
3 Bedrooms
1 Bath
10 Guests
988 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
AU $909/Night
7 Nights - AU $6,366
House
9.8(7 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
AU $1,182/Night
7 Nights - AU $8,278
New
House
9.6(69 Reviews)
6 Bedrooms
4 Baths
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $1,258/Night
7 Nights - AU $8,807
Why Choose Rent By Owner for your Middleborough Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Middleborough
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you enjoy the region's unique atmosphere and make the most of your vacation experience, whether you're seeking outdoor activities or tranquil retreats in this destination.
Peak Season Highlights
Summer (June to August)
During the summer months, the region experiences warm weather that is ideal for exploring outdoor activities and enjoying the natural beauty of this destination.
Average Temperature Daytime: around 80°F to 85°F - Nighttime: about 60°F to 65°F
Fall (September to November)
In early fall, the area boasts vibrant foliage and comfortable temperatures, perfect for outdoor adventures and scenic drives during this popular season.
Average Temperature Daytime: roughly 70°F to 75°F - Nighttime: around 50°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler weather, offering a peaceful time to enjoy the region's quiet charm away from peak tourist crowds.
Average Temperature Daytime: approximately 30°F to 40°F - Nighttime: near 20°F to 25°F
Spring (March to May)
Early spring sees milder conditions and blooming scenery, making it an ideal time for those seeking fewer visitors and a more relaxed experience.
Average Temperature Daytime: around 50°F to 60°F - Nighttime: close to 35°F to 45°F
Weekly Weather Forecast for Middleborough
How to Book Your Middleborough Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor dining area perfect for meals amidst the fresh air.
- Relax by a charming outdoor fireplace or fire pit during cool evenings.
- Take advantage of spacious yards that are ideal for outdoor activities and play.
- Make use of well-maintained patios or decks for entertaining guests.
- Benefit from access to scenic walking trails or pathways nearby.
- Unwind in a tranquil garden setting with lush landscaping and seating areas.
- Utilize outdoor grills or BBQ stations to prepare delicious meals during your stay.
Top Attractions Around Middleborough
What attractions are nearby?
While staying here, you can explore a variety of outdoor activities and scenic spots nearby that showcase the natural beauty and cultural charm of the region.
Family Activities
- Middleborough Recreation Department: Engage in numerous family-friendly outdoor activities, including sports, playgrounds, and community events right here in the area.
- Heritage Park: Enjoy a leisurely day exploring walking trails, picnicking spots, and scenic views perfect for quality family time amidst nature.
- Pilgrim Memorial State Park: Discover this historic park that offers educational exhibits and outdoor space ideal for family outings near the region's rich history.
- Local Farm Tours: Experience hands-on farm activities and learn about regional agriculture, making for an entertaining and educational day for all ages.
Adult Activities
- Explore the local history at the Middleborough Historical Museum: Dive into the area's rich heritage through engaging exhibits that bring its past to life.
- Enjoy outdoor recreation at the Basse Farm Conservation Area: Experience scenic walking trails and tranquil nature surroundings perfect for a relaxing day outdoors.
- Visit the nearby wildlife refuges: Observe native bird species and enjoy nature photography in peaceful, preserved habitats close to here.
- Participate in cultural events at local community centers: Engage with regional traditions and festivities that showcase the region's vibrant local culture.
Other Places to Stay in Middleborough, MA
Robbins Museum
SMG Middleboro Family Practice
Middleborough Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the area's event calendar before your trip to align your stay with local festivals or gatherings that can enrich your experience here.
- Explore Natural Landscapes: Take advantage of the region’s outdoor spaces for activities like hiking or relaxing in scenic spots, enhancing your connection to this destination’s natural beauty.
- Discover Nearby Dining Options: Research local restaurants and eateries to enjoy authentic regional cuisine and support small businesses during your visit.
- Use Local Transportation: Familiarize yourself with available transportation options to navigate efficiently and make the most of your time exploring here.
Transportation Options
- Middleborough Transit Station: This regional hub offers convenient bus services that connect you to nearby cities and transportation networks.
- Massachusetts Bay Transportation Authority (MBTA): Accessible from here, the MBTA provides commuter rail and bus options to explore Greater Boston and beyond.
- Rental Car Services: Several rental agencies operate in the area, giving you flexible transportation choices during your stay.
- Local Taxi and Ride-Sharing Services: Reliable taxi companies and ride-sharing options are available for easy, door-to-door travel within the region.
Local Customs Options
- Stone Soup Festival: Celebrated here, this local tradition highlights community spirit through a communal meal that showcases regional cuisine and fosters togetherness.
- Historical Preservation Practices: Respect for the area's colonial past is evident in the preservation of historic sites and architecture, offering you a glimpse into its rich history.
- Traditional New England Celebrations: Seasonal events like fall festivals and holiday parades reflect the region’s cultural heritage and provide authentic local experiences.
- Community Farmer's Markets: Engaging with local farmers at these markets allows you to enjoy fresh, regional produce while supporting sustainable agriculture in the area.
Frequently Asked Questions About Middleborough?
1. What are the top vacation rentals in Middleborough?
There are a lot of options in Middleborough. If you plan on staying in the Middleborough area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middleborough:
- Excellent Reviews: 500 ft to beach and central air conditioning!
- New England Lake Cottage On Long Pond on over 20 Wooded Acres
- Charming cottage on the water with beautiful views
- Charming Converted Carriage House, Historic Downtown near Harbor
- Downtown! Cultural District, One Block to Yacht Club and Harbor
- HEART of downtown! Walk to beach, shops, restaurants & steps to the harbor!
- Historic Charm Meets Coastal Comfort – Steps from Downtown Plymouth
- 3 Bedroom Home Facing Inner harbor with 1st Floor King Bedroom.
- Cozy Lake Front Cottage on Long Pond
- NEW HOME 3/23. Walk to Town; Restaurants, Water & Sites!
2. How many vacation rentals have private pools in Middleborough?
There are 14 vacation rentals with private pools near Middleborough. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Middleborough are best for families?
If you are looking for a family-friendly vacation home in Middleborough, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middleborough:
4. How many Rentbyowner vacation rentals are available in Middleborough?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 312 in the Middleborough area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Middleborough.
5. What is the cancellation policy for a vacation rental in this area?
Cancellation policies vary by property, so you should review the specific listing details or contact the property owner directly to understand the terms applicable to your booking.
6. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning, service charges, or security deposits are often listed on each property’s page. To ensure transparency, check the detailed listing or reach out to the owner for clarification.
7. How do I confirm my reservation and what payment methods are accepted?
Reservations are confirmed once all required payments are processed through the booking platform. Accepted payment options typically include credit cards and other secure payment methods specified on the listing.
8. What amenities can I expect in vacation rentals around here?
Amenities will vary by property, but common features may include Wi-Fi, parking, kitchen facilities, and outdoor spaces. For precise amenities, review the property details or contact the host directly.
9. Is it possible to modify or extend my stay after booking?
Modifications and extensions depend on the property's policies and availability. Contact the property owner directly to discuss possible changes to your reservation.
Middleborough Top Rated Vacation Rentals
Hotel
9.4(904 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Balcony/Terrace
AU $248/Night
7 Nights - AU $1,739
AU $283/Night
7 Nights - AU $1,980
AU $221/Night
7 Nights - AU $1,545
AU $228/Night
7 Nights - AU $1,597
Hotel
9.0(754 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
AU $349/Night
7 Nights - AU $2,441
Hotel
9.0(543 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
AU $365/Night
7 Nights - AU $2,553
Apartment
9.0(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
1194.79 ft²
- Parking
- Pool
- Air Conditioner
- Child Friendly
AU $308/Night
7 Nights - AU $2,156
Hotel
8.9(136 Reviews)
6 Baths
556.14 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
AU $247/Night
7 Nights - AU $1,729
