Best Vacation Homes in Middleborough
New
House
3 Bedrooms
1 Bath
6 Guests
Fireplace/Heating
Air Conditioner
Internet
Security/Safety
£815/Night
7 Nights - £5,707
Apartment
10.0(3 Reviews)
1 Bedroom
2 Baths
2 Guests
796.53 ft²
- Fireplace/Heating
Parking- Internet
Child Friendly
£144/Night
7 Nights - £1,007
Bed & Breakfast
9.2(72 Reviews)
1 Bedroom
1 Bath
Hot Tub- Fireplace/Heating
Balcony/Terrace
Breakfast
£74/Night
7 Nights - £515
Cottage
10.0(45 Reviews)
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
£181/Night
7 Nights - £1,270
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
- Fireplace/Heating
Pet Friendly- Parking
- Internet
£156/Night
7 Nights - £1,089
Apartment
10.0(42 Reviews)
2 Bedrooms
1 Bath
4 Guests
650 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
£185/Night
7 Nights - £1,293
House
10.0(33 Reviews)
2 Bedrooms
1 Bath
4 Guests
1301 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£361/Night
7 Nights - £2,530
Cottage
10.0(21 Reviews)
3 Bedrooms
1 Bath
8 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£282/Night
7 Nights - £1,972
Middleborough Luxury Rentals
House
10.0(5 Reviews)
5 Bedrooms
5 Baths
12 Guests
5307 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£1,871/Night
7 Nights - £13,094
House
10.0(7 Reviews)
7 Bedrooms
7 Baths
25 Guests
9300 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
£1,496/Night
7 Nights - £10,472
House
6 Bedrooms
4 Baths
15 Guests
3993.41 ft²
- Fireplace/Heating
View- Pet Friendly
- Air Conditioner
£1,439/Night
7 Nights - £10,072
Hotel
9.7(17 Reviews)
7 Baths
282.94 ft²
- Balcony/Terrace
- View
- Parking
- Air Conditioner
£1,264/Night
7 Nights - £8,851
House
4 Bedrooms
2 Baths
8 Guests
3993.41 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Air Conditioner
£986/Night
7 Nights - £6,902
House
9.8(14 Reviews)
3 Bedrooms
1 Bath
10 Guests
1800 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
£933/Night
7 Nights - £6,534
House
6 Bedrooms
4 Baths
15 Guests
3993 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£849/Night
7 Nights - £5,940
Middleborough Pet Friendly Vacation Rentals
Apartment
10.0(18 Reviews)
3 Bedrooms
2 Baths
8 Guests
1615 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£464/Night
7 Nights - £3,246
Apartment
9.5(4 Reviews)
1 Bedroom
1 Bath
6 Guests
452.08 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
£120/Night
7 Nights - £839
Hotel
7.2(1005 Reviews)
1 Bath
Pool- Breakfast
- Pet Friendly
- Kitchen
£77/Night
7 Nights - £540
Apartment
10.0(9 Reviews)
3 Bedrooms
2 Baths
8 Guests
1722 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£523/Night
7 Nights - £3,659
Apartment
9.5(2 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
£120/Night
7 Nights - £839
Apartment
10.0(7 Reviews)
2 Bedrooms
2 Baths
9 Guests
1722 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£568/Night
7 Nights - £3,975
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
1025 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£267/Night
7 Nights - £1,868
Apartment
10.0(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
1722 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£549/Night
7 Nights - £3,846
Middleborough Large Vacation Homes
House
10.0(37 Reviews)
5 Bedrooms
1 Bath
7 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£454/Night
7 Nights - £3,180
House
10.0(1 Review)
1 Bedroom
4 Baths
12 Guests
- Parking
- Child Friendly
Barbecue/Outdoor Cooking
£523/Night
7 Nights - £3,663
House
10.0(31 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£314/Night
7 Nights - £2,201
Bed & Breakfast
9.8(95 Reviews)
3 Bedrooms
3 Baths
12 Guests
516.67 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Ocean View
£176/Night
7 Nights - £1,230
House
10.0(20 Reviews)
4 Bedrooms
3 Baths
10 Guests
3047 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£737/Night
7 Nights - £5,161
House
Expansive Cape Cod Retreat in Wareham: Modern Amenities and Traditional Charm with Private Courtyard
10.0(12 Reviews)
3 Bedrooms
1 Bath
12 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£406/Night
7 Nights - £2,845
House
10.0(9 Reviews)
5 Bedrooms
3 Baths
12 Guests
2800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£745/Night
7 Nights - £5,213
House
10.0(2 Reviews)
6 Bedrooms
3 Baths
12 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Internet
£780/Night
7 Nights - £5,460
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.
Explore and book the perfect rental in Middleborough
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!
- Incredible Townhouse 2 blocks to Harbor, SubZero kitchen, Architectural Detail
- The Mojito House with Hot Tub, Arcade and Theatre walking distance downtown
- Peaceful, Rustic Retreat, 100ft of Private Beach, 300 Acre Sandy Bottom Pond
- 3 Bedroom Home Facing Inner harbor with 1st Floor King Bedroom.
2. How many vacation rentals have private pools in Middleborough?
There are 12 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 291 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
House
9.8(7 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
£460/Night
7 Nights - £3,219
Hotel
9.4(865 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
£132/Night
7 Nights - £925
Hotel
9.0(1004 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
£100/Night
7 Nights - £702
£101/Night
7 Nights - £708
Hotel
9.0(729 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
£139/Night
7 Nights - £971
Hotel
9.0(530 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
£122/Night
7 Nights - £855
Hotel
9.0(139 Reviews)
4 Baths
355.21 ft²
Private Pool- Fireplace/Heating
- Pool
- Pet Friendly
£143/Night
7 Nights - £1,002
Apartment
9.0(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
1194.79 ft²
- Pool
- Parking
- Air Conditioner
- Child Friendly
£159/Night
7 Nights - £1,111
