Best Vacation Homes in Middleton
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
ZA R2,470/Night
For 7 Nights ZA R17,298
398.26 ft²
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Fireplace/Heating
- Parking
- Internet
ZA R3,879/Night
For 7 Nights ZA R27,152
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
ZA R2,255/Night
For 7 Nights ZA R15,780
1500 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R4,669/Night
For 7 Nights ZA R32,682
2152.78 ft²
10 Guests
4 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Parking
- Internet
ZA R13,469/Night
For 7 Nights ZA R94,282
593 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R3,924/Night
For 7 Nights ZA R27,466
1700 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
ZA R3,688/Night
For 7 Nights ZA R25,815
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R3,536/Night
For 7 Nights ZA R24,742
Middleton Luxury Rentals
355.21 ft²
28 Guests
84 Bedrooms
1 Bathroom
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R17,100/Night
For 7 Nights ZA R119,701
2153 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R11,284/Night
For 7 Nights ZA R78,997
2750 ft²
11 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R8,450/Night
For 7 Nights ZA R59,157
9 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
House
- Internet
- Child Friendly
- Security/Safety
ZA R7,713/Night
For 7 Nights ZA R53,991
2568 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R6,969/Night
For 7 Nights ZA R48,791
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
ZA R6,545/Night
For 7 Nights ZA R45,820
6 Guests
3 Bedrooms
1 Bathroom
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
ZA R6,510/Night
For 7 Nights ZA R45,573
6 Guests
3 Bedrooms
1 Bathroom
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
ZA R6,242/Night
For 7 Nights ZA R43,691
Middleton Pet Friendly Vacation Rentals
4 Guests
2 Bedrooms
1 Bathroom
Couples Retreat
House
- Fireplace/Heating
- Pet Friendly
- Internet
ZA R5,857/Night
For 7 Nights ZA R41,001
419.79 ft²
21 Guests
96 Bedrooms
4 Bathrooms
Free Cancellation
Hotel
- Oceanfront
- Fireplace/Heating
- Pool
ZA R3,890/Night
For 7 Nights ZA R27,235
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
ZA R9,952/Night
For 7 Nights ZA R69,655
900 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
ZA R4,148/Night
For 7 Nights ZA R29,034
214.45 ft²
39 Guests
151 Bedrooms
1 Bathroom
Ocean View
Hotel
- Oceanfront
- Fireplace/Heating
- Pool
ZA R5,284/Night
For 7 Nights ZA R36,990
600 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
ZA R2,966/Night
For 7 Nights ZA R20,764
215 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
ZA R4,075/Night
For 7 Nights ZA R28,522
430 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
ZA R9,605/Night
For 7 Nights ZA R67,229
Middleton Large Vacation Homes
9 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Air Conditioner
- Child Friendly
- Laundry
ZA R10,976/Night
For 7 Nights ZA R76,835
860 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
ZA R17,828/Night
For 7 Nights ZA R124,801
860 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
ZA R16,741/Night
For 7 Nights ZA R117,192
645 ft²
12 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
ZA R13,975/Night
For 7 Nights ZA R97,831
645 ft²
12 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
ZA R13,183/Night
For 7 Nights ZA R92,285
3200 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Kitchen
- Air Conditioner
- Internet
ZA R15,351/Night
For 7 Nights ZA R107,454
Why Choose Rent By Owner for your Middleton 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 Middleton
When should you plan your Vacation Rentals stay?
Timing your visit to Middleton is key to enjoying the best weather and local events, making it easier to find the perfect vacation rental in this charming New England destination.
Peak Season Highlights
Summer (June to August)
During the summer months, you'll experience warm and inviting weather, ideal for enjoying outdoor activities and exploring the local scenery.
Average Temperature Daytime: around 75°F to 85°F - Nighttime: about 60°F to 65°F
Fall (September to November)
This time of year offers beautiful foliage and mild temperatures, making it a perfect season for scenic drives and outdoor adventures in the area.
Average Temperature Daytime: roughly 65°F to 75°F - Nighttime: near 50°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler weather, but it's an excellent season for those seeking quieter surroundings and cozy stays in this destination.
Average Temperature Daytime: about 30°F to 40°F - Nighttime: around 20°F to 25°F
Early Spring (March to April)
As the region transitions into spring, you can enjoy fewer crowds and the early signs of blooming nature, perfect for relaxed outdoor exploration.
Average Temperature Daytime: approximately 45°F to 55°F - Nighttime: around 35°F to 45°F
Weekly Weather Forecast for Middleton
How to Book Your Middleton 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 Middleton
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 outdoor dining with a fully equipped patio or barbecue area.
- Take advantage of private gardens or landscaped yards for relaxation and leisure.
- Make use of a spacious deck or porch to soak in the scenic surroundings.
- Explore nearby hiking or walking trails accessible directly from your rental.
- Relax by an outdoor fire pit, perfect for evening gatherings.
- Benefit from access to outdoor recreational facilities such as tennis courts or swimming pools, if available.
- Experience privacy with fenced yards, ideal for outdoor activities or family gatherings.
Top Attractions Around Middleton
What attractions are nearby?
Within this charming region, you can enjoy a variety of outdoor activities and local attractions that highlight the area's natural beauty and cultural heritage, making your stay both relaxing and memorable.
Family Activities
- Maudslay State Park: Enjoy outdoor adventures as you explore scenic walking trails, picnic areas, and lush gardens perfect for family outings within this natural haven.
- Game On Family Fun Center: Experience hours of entertainment with arcade games, laser tag, and interactive activities designed to keep children engaged and active in a lively setting.
- Sea Festival at the Waterfront: Attend seasonal events and festivities at the waterfront, offering family-friendly entertainment, music, and local food vendors in a vibrant environment.
- Middleton Historical Society Museum: Discover the area's rich history through interactive exhibits and guided tours that provide an educational experience for visitors of all ages.
Adult Activities
- Visiting the Bradley Palmer State Park: Enjoy outdoor activities like hiking, biking, and exploring scenic nature trails within this expansive state park nearby.
- Exploring local history at the Middleton Town Museum: Discover the rich heritage of the area through engaging exhibits and historical artifacts that tell the story of this destination.
- Dining at local eateries in Middleton village: Savor regional flavors and fresh local ingredients at charming restaurants that capture the essence of the region’s culinary scene.
- Shopping at nearby artisan markets: Browse unique handmade crafts, antiques, and local produce to experience the creative spirit of the community here.
Other Places to Stay in Middleton, MA
CoCo Key Water Resort - Boston
Middleton Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Shopping: Take advantage of the area's charming eateries and boutique shops to experience authentic local flavors and crafts during your stay.
- Plan Outdoor Activities: Make the most of the region's natural beauty by scheduling outdoor pursuits like hiking, biking, or relaxing in nearby parks.
- Discover Nearby Cultural Events: Check out community events and festivals that showcase the area's rich traditions and vibrant arts scene, enriching your visit.
- Choose a Well-Located Vacation Rental: Select a property close to key attractions and amenities to maximize convenience and immersion in this destination's local ambiance.
Transportation Options
- Boston Logan International Airport: This major airport offers convenient domestic and international flights, making it an accessible gateway for travelers visiting the area.
- Newburyport Rail Station: You can easily access Amtrak and commuter rail services here to reach nearby cities and explore the region by train.
- Local Taxi and Ride-Sharing Services: Reliable taxi companies and ride-sharing options provide flexible transportation throughout this destination and its surroundings.
- Regional Bus Services: Bus routes connecting Middleton to neighboring towns and attractions offer an affordable and practical way to get around the region.
Local Customs Options
- Greeting the Community: Locals in the area often exchange friendly greetings like "Hello" or "Good morning," reflecting the welcoming spirit you can experience during your stay.
- Seasonal Festivals: Participating in seasonal celebrations is common here, offering you a chance to immerse yourself in regional traditions and community gatherings.
- Local Dining Etiquette: It’s customary to enjoy meals together with appreciation for locally sourced ingredients, showcasing the region's culinary pride.
- Respect for Nature: Residents prioritize environmental preservation, encouraging visitors to practice responsible outdoor activities and leave no trace behind.
Frequently Asked Questions About Middleton?
1. What are the top vacation rentals in Middleton?
There are a lot of options in Middleton. If you plan on staying in the Middleton area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middleton:
- Luxury and Modern Apt near Mall/Hospital
- Large, Comfortable & Conveniently located Home
- Danvers spacious apt near Salem historic witch town Mall/Hospital
- Near Phillips Academy Andover.
- Cozy house, close to downtown Danvers
- Charming Apartment in historic 1800's home
- Tranquil guest house in Boxford perfect for a relaxing getaway. with hottub.
- house close to Phillips academy and down town
- Phillips Academy Area – Ideal for Families Visiting Campus & Touring New England
- 5 Mi to Salem: Furnished Patio at Danvers Studio!
2. How many vacation rentals have private pools in Middleton?
There are 2 vacation rentals with private pools near Middleton. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Middleton are best for families?
If you are looking for a family-friendly vacation home in Middleton, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middleton:
4. How many Rentbyowner vacation rentals are available in Middleton?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 83 in the Middleton 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 Middleton.
5. What is the cancellation policy for vacation rentals here in Middleton, Massachusetts?
Cancellation policies vary depending on the property. You should review the specific listing details or contact the host directly to understand the cancellation terms before booking.
6. Are there any additional fees I should be aware of when booking a vacation rental in this region?
Additional fees such as cleaning fees, service charges, or taxes are often included in the listing details. It's best to check the listing specifics or communicate with the property owner for a complete fee breakdown.
7. How do I confirm my reservation and what is the process for checking in?
Reservation confirmation and check-in procedures are outlined in the property's listing. You may need to coordinate with the host for key exchange or access instructions, which ensures a smooth arrival experience.
8. Can I find pet-friendly vacation rentals in this area, and are there any restrictions?
Many properties in this destination accommodate pets, but each has its own rules. Check the listing details for pet policies, restrictions, and any additional fees that may apply.
9. What amenities are typically available in vacation rentals here in the region?
Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and parking. Review the individual listing to confirm which amenities are offered during your stay.
Middleton Top Rated Vacation Rentals
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
ZA R3,300/Night
For 7 Nights ZA R23,108
322.92 ft²
20 Guests
134 Bedrooms
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
ZA R2,973/Night
For 7 Nights ZA R20,814
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
ZA R1,950/Night
For 7 Nights ZA R13,650
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
ZA R2,194/Night
For 7 Nights ZA R15,351
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Spa
- Pool
- Breakfast
ZA R2,137/Night
For 7 Nights ZA R14,954
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
ZA R2,253/Night
For 7 Nights ZA R15,763
305.7 ft²
18 Guests
117 Bedrooms
3 Bathrooms
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
ZA R3,106/Night
For 7 Nights ZA R21,738
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Breakfast
ZA R1,630/Night
For 7 Nights ZA R11,406
