Best Vacation Homes in Middleton
Apartment
1 Bedroom
1 Bath
2 Guests
Fireplace/Heating
Air Conditioner
Internet
Child Friendly
US $185/Night
7 Nights - US $1,298
Apartment
8.8(24 Reviews)
1 Bedroom
1 Bath
2 Guests
398.26 ft²
- Fireplace/Heating
Parking- Internet
- Child Friendly
US $235/Night
7 Nights - US $1,645
US $177/Night
7 Nights - US $1,236
Apartment
10.0(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
1500 ft²
- Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $283/Night
7 Nights - US $1,980
House
4 Bedrooms
3 Baths
10 Guests
2152.78 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $816/Night
7 Nights - US $5,712
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
593 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $240/Night
7 Nights - US $1,679
House
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1700 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $225/Night
7 Nights - US $1,575
Apartment
9.8(24 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $223/Night
7 Nights - US $1,562
Middleton Luxury Rentals
Hotel
7.3(391 Reviews)
1 Bath
355.21 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $1,036/Night
7 Nights - US $7,252
House
9.8(72 Reviews)
4 Bedrooms
2 Baths
11 Guests
2750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $557/Night
7 Nights - US $3,896
House
10.0(51 Reviews)
4 Bedrooms
2 Baths
8 Guests
2568 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $512/Night
7 Nights - US $3,581
House
3 Bedrooms
2 Baths
9 Guests
- Internet
- Child Friendly
Security/Safety
US $509/Night
7 Nights - US $3,562
Apartment
10.0(56 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $479/Night
7 Nights - US $3,354
House
9.6(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
2153 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $475/Night
7 Nights - US $3,323
Apartment
10.0(38 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $447/Night
7 Nights - US $3,131
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $410/Night
7 Nights - US $2,867
Middleton Pet Friendly Vacation Rentals
House
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Internet
- Child Friendly
US $319/Night
7 Nights - US $2,232
House
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $603/Night
7 Nights - US $4,220
House
9.4(52 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
Pool
Ocean View
View
US $251/Night
7 Nights - US $1,759
House
9.4(3 Reviews)
1 Bedroom
1 Bath
4 Guests
600 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $161/Night
7 Nights - US $1,125
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
215 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $247/Night
7 Nights - US $1,728
House
2 Bedrooms
2 Baths
8 Guests
430 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $582/Night
7 Nights - US $4,073
Middleton Large Vacation Homes
House
5 Bedrooms
4 Baths
9 Guests
- Air Conditioner
- Child Friendly
Laundry
Bedding/Linens
US $665/Night
7 Nights - US $4,655
House
4 Bedrooms
4 Baths
16 Guests
860 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $1,080/Night
7 Nights - US $7,561
House
4 Bedrooms
4 Baths
16 Guests
860 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $1,014/Night
7 Nights - US $7,100
House
3 Bedrooms
3 Baths
12 Guests
645 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $847/Night
7 Nights - US $5,927
House
3 Bedrooms
3 Baths
12 Guests
645 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $799/Night
7 Nights - US $5,591
House
4.8(6 Reviews)
4 Bedrooms
3 Baths
12 Guests
3200 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $930/Night
7 Nights - US $6,510
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.
Middleton Vacation Rental Frequently Asked Questions
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
- 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!
- 10 Mi to Crane Beach: Wooded Home Near Boston!
2. How many vacation rentals have private pools in Middleton?
There are 3 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 85 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
Hotel
9.0(1009 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $137/Night
7 Nights - US $956
Hotel
9.0(714 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $178/Night
7 Nights - US $1,243
Hotel
8.9(102 Reviews)
4 Baths
419.79 ft²
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
US $236/Night
7 Nights - US $1,650
Hotel
8.7(1010 Reviews)
1 Bath
322.92 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $180/Night
7 Nights - US $1,261
Hotel
8.6(1015 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $140/Night
7 Nights - US $978
US $143/Night
7 Nights - US $1,004
US $129/Night
7 Nights - US $906
Hotel
8.1(629 Reviews)
1 Bath
214.45 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $320/Night
7 Nights - US $2,241
