Best Vacation Homes in Middlesex County
9 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $2,804/Night
For 7 Nights US $19,628
1097.92 ft²
8 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $684/Night
For 7 Nights US $4,788
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $151/Night
For 7 Nights US $1,057
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $964/Night
For 7 Nights US $6,751
538.2 ft²
2 Guests
1 Bedroom
1 Bathroom
House
- Balcony/Terrace
- Kitchen
- Parking
US $125/Night
For 7 Nights US $875
4000 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $917/Night
For 7 Nights US $6,421
1800 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $855/Night
For 7 Nights US $5,985
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $816/Night
For 7 Nights US $5,713
Middlesex County Luxury Rentals
2450 ft²
22 Guests
9 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $6,594/Night
For 7 Nights US $46,155
8 Guests
4 Bedrooms
2 Bathrooms
Group Friendly
House
- Parking
- Internet
- Child Friendly
US $4,479/Night
For 7 Nights US $31,352
2002.09 ft²
24 Guests
8 Bedrooms
9 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $4,098/Night
For 7 Nights US $28,686
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Ocean View
US $3,692/Night
For 7 Nights US $25,844
12916.69 ft²
24 Guests
8 Bedrooms
9 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Parking
US $3,546/Night
For 7 Nights US $24,822
1248.61 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- View
- Pet Friendly
US $3,357/Night
For 7 Nights US $23,497
2139.87 ft²
122 Guests
33 Bedrooms
34 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $3,267/Night
For 7 Nights US $22,867
4000 ft²
14 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $3,144/Night
For 7 Nights US $22,008
Middlesex County Pet Friendly Vacation Rentals
11 Guests
5 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $510/Night
For 7 Nights US $3,573
1001.04 ft²
5 Guests
8 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $433/Night
For 7 Nights US $3,031
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $160/Night
For 7 Nights US $1,118
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $438/Night
For 7 Nights US $3,065
1001.04 ft²
5 Guests
17 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $901/Night
For 7 Nights US $6,304
829 ft²
4 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $375/Night
For 7 Nights US $2,625
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $347/Night
For 7 Nights US $2,430
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $244/Night
For 7 Nights US $1,710
Middlesex County Large Vacation Homes
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $723/Night
For 7 Nights US $5,060
592.02 ft²
4 Guests
7 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $341/Night
For 7 Nights US $2,385
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $694/Night
For 7 Nights US $4,859
1055 ft²
5 Guests
6 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Private Pool
- Fireplace/Heating
- Pool
US $606/Night
For 7 Nights US $4,242
2400.35 ft²
10 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Balcony/Terrace
- View
- Parking
US $895/Night
For 7 Nights US $6,265
603 ft²
4 Guests
5 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Private Pool
- Fireplace/Heating
- Pool
US $476/Night
For 7 Nights US $3,332
990 ft²
5 Guests
6 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Private Pool
- Fireplace/Heating
- Pool
US $455/Night
For 7 Nights US $3,185
1000 ft²
12 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Hot Tub
- Fireplace/Heating
- Pool
US $1,696/Night
For 7 Nights US $11,870
Why Choose Rent By Owner for your Middlesex County 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 Middlesex County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as seasonal weather patterns and local events in Middlesex County influence the best periods for enjoying your stay.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you can enjoy mild weather and lush scenery as the region transitions into summer, making it ideal for exploring outdoor activities and local attractions.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Early Fall (September to October)
This season offers comfortable temperatures and beautiful fall foliage, providing a picturesque backdrop for your stay while experiencing the area's vibrant seasonal colors.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler temperatures, but the region's quiet atmosphere can be perfect for a cozy retreat and avoiding crowds, ideal for those seeking tranquility and indoor activities.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
Early Spring (March to April)
As the area begins to thaw, you'll experience fewer tourists and lower prices, making it a worthwhile time for budget-conscious travelers interested in exploring without the peak-season crowds.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Middlesex County
How to Book Your Middlesex County 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 Middlesex County
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 space with a furnished patio or deck for relaxing and entertaining.
- Take advantage of lush gardens or landscaped yards that add beauty and tranquility to your stay.
- Make the most of outdoor dining areas perfect for meals al fresco during warm weather.
- Utilize a grill or outdoor kitchen for convenient barbecues and cookouts in the region’s inviting climate.
- Spend time on well-maintained lawns suitable for outdoor games and activities.
- Explore nearby walking trails, bike paths, or parks accessible directly from the property.
- Relax by an outdoor swimming pool or hot tub, common features in many vacation rentals here.
Top Attractions Around Middlesex County
What attractions are nearby?
In this region, you can explore a variety of outdoor activities, cultural sites, and scenic parks that provide the perfect setting for an enjoyable stay in Middlesex County, Massachusetts.
Family Activities
- Harvard Museum of Natural History: Discover fascinating exhibits and interactive displays that will engage every member of the family here in Middlesex County.
- Minute Man National Historical Park: Step back into history with outdoor trails and historic sites that provide educational fun for all ages in this part of the region.
- Children’s Discovery Museum of Science: Ignite curiosity with hands-on science activities and engaging exhibits designed specifically for young explorers in this destination.
- Great Brook Farm State Park: Enjoy outdoor adventures like hiking, picnicking, and seasonal activities amidst scenic farmland and open spaces in the area.
Adult Activities
- Visit the Minuteman National Historical Park: Immerse yourself in American history as you explore the historic sites and trails dedicated to the beginning of the Revolutionary War.
- Explore the Boston Public Market: Savor local flavors and artisanal products at this bustling marketplace, perfect for food lovers seeking authentic regional cuisine.
- Enjoy outdoor activities along the Charles River: Whether kayaking, paddleboarding, or walking along scenic pathways, this area offers a variety of relaxing ways to experience the outdoors.
- Discover local art at the Middlesex Fells Reservation: Engage with nature and culture through hiking or simply appreciating the outdoor sculptures and natural beauty nestled within this expansive parkland.
Other Places to Stay in Middlesex County, MA
Cambridge
Somerville
Arefth
East Cambridge
Everett
Central Square
The Port
Waltham
Medford
Woburn
Winter Hill
The Lanes
Middlesex County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take advantage of nearby cultural sites and parks to immerse yourself in the region's rich history and natural beauty.
- Plan Your Transportation: Arrange convenient transportation options in advance to easily access popular destinations within this area.
- Choose the Right Accommodation: Select a vacation rental that offers comfort and amenities suited to your travel plans for a more enjoyable stay here.
- Discover Hidden Gems: Talk to locals or seek out lesser-known spots to experience the authentic charm of the region beyond typical tourist sites.
Transportation Options
- Massachusetts Bay Transportation Authority (MBTA): You can rely on the MBTA for comprehensive subway, bus, and commuter rail services connecting various towns and cities within the region, making it easy to explore here without a car.
- Amtrak Rail Services: Useful for longer-distance travel, Amtrak connects this area to major cities across the country, providing a convenient option for those looking to venture further afield.
- Regional Bus Services: Local and regional buses operate throughout here, offering affordable transportation options to access different neighborhoods and nearby attractions.
- Private Transportation and Rideshare Services: Companies like Uber and Lyft are readily available here, giving you flexible, on-demand travel options during your stay in this part of Massachusetts.
Local Customs Options
- Tea Party Celebrations: Participating in the area's historic events often involves observing or engaging in traditional Tea Party celebrations that commemorate the region's pivotal role in American history.
- Local Seafood Cuisine: You’ll find that savoring fresh seafood dishes is a cherished custom, reflecting the region’s maritime heritage and making it an essential part of your visit experience.
- Historic Preservation Practices: Respect for historical sites and active preservation efforts are deeply ingrained here, encouraging visitors to appreciate and support the area’s rich past.
- Community Festivals: Attending seasonal festivals showcases the community spirit and local traditions, offering authentic interactions with residents and their cultural heritage.
Frequently Asked Questions About Middlesex County?
1. What are the top vacation rentals in Middlesex County?
There are a lot of options in Middlesex County. If you plan on staying in the Middlesex County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middlesex County:
- Near Boston Historic two-bedroom with Modern Amenities
- Fun, Family Friendly Restored Fire House 2 Bedroom Apt
- 5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.
- 3 BR/3 BATH in Historic Home Mins from Kendall Sq , MIT, Harvard, Boston.
- The Inn at Newton Highlands, boutique apartment-hotel
- The Inn at Newton Highlands, boutique apartment-hotel
- Wonderfully renovated family-friendly home located near Boston and Lexington
- Super Family-Friendly! Spacious, cozy home base - close to Boston & Salem MA!
- A Village Bed and Breakfast
- Mid Century in Historic Lexington
2. How many vacation rentals have private pools in Middlesex County?
There are 69 vacation rentals with private pools near Middlesex County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Middlesex County are best for families?
If you are looking for a family-friendly vacation home in Middlesex County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middlesex County:
4. How many Rentbyowner vacation rentals are available in Middlesex County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 2290 in the Middlesex County 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 Middlesex County.
5. What is the cancellation policy for properties in Middlesex County, Massachusetts?
Cancellation policies vary depending on the specific vacation rental you choose. You should review the property's listing details or contact the owner directly to understand the applicable cancellation terms and any potential fees.
6. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning, service charges, or security deposits are often outlined in the property listing. It’s recommended to read the full description carefully or reach out to the host for clarification before confirming your reservation.
7. How do I confirm the availability of a vacation rental in Middlesex County?
Availability can be checked through the property’s online calendar or by contacting the owner directly. Ensure your travel dates are flexible, or specify your preferred dates when making an inquiry.
8. What amenities are typically included in vacation rentals here?
Most vacation rentals offer essential amenities such as Wi-Fi, parking, and kitchen facilities. However, specific features may vary, so it’s best to review each listing detail or ask the owner about any particular amenities you need during your stay.
9. How do I ensure a smooth check-in process at my chosen vacation rental in this region?
Check the listing for detailed check-in instructions provided by the owner, which might include key pickup or digital lock access. Contact the host if you have any special requests or need further assistance prior to your arrival.
Middlesex County Top Rated Vacation Rentals
1200 ft²
5 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $372/Night
For 7 Nights US $2,604
2000 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $637/Night
For 7 Nights US $4,461
9 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,340/Night
For 7 Nights US $9,383
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $270/Night
For 7 Nights US $1,890
4000 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $829/Night
For 7 Nights US $5,801
1001 ft²
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Private Pool
- Fireplace/Heating
- Pool
US $446/Night
For 7 Nights US $3,123
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Pool
US $205/Night
For 7 Nights US $1,437
2700 ft²
6 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $377/Night
For 7 Nights US $2,642
