Middleton holiday homes

We found 503 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Middleton to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, such as Wi-Fi and cable TV. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Middleton

Showing deals for:29 Jan - 5 Feb

Kitchen
Exceptional
(17 reviews)

Whole house rental. 12 min to amazing Crane Beach

Ipswich

8% off
NZ$5,107
for 7 nights, 1 home
NZ$730 per night
includes taxes & fees
Whole house rental. 12 min to amazing Crane Beach
Dining
Exceptional
(57 reviews)

Beautiful Victorian with Modern Flare close to Town, Train & Beach

Ipswich

7% off
NZ$2,015
for 7 nights, 1 apartment
NZ$288 per night
includes taxes & fees
Beautiful Victorian with Modern Flare close to Town, Train & Beach
Exterior detail
Exceptional
(36 reviews)

The Anchor House Marblehead Retreat - Minutes to Old Town and Historic Salem!

Marblehead

12% off
NZ$6,162
for 7 nights, 1 home
NZ$880 per night
includes taxes & fees
The Anchor House Marblehead Retreat - Minutes to Old Town and Historic Salem!
Side of the house
Wonderful
(7 reviews)

Spacious 2BR Apartment Near Bradford & Merrimack Valley Parking Included.

Haverhill

8% off
NZ$2,703
for 7 nights, 1 apartment
NZ$386 per night
includes taxes & fees
Spacious 2BR Apartment Near Bradford & Merrimack Valley Parking Included.
Interior
Exceptional
(6 reviews)

2 Bed, 1.5 Bath Stunning Apartment, Central Andover Location

Andover

12% off
NZ$7,060
for 7 nights, 1 apartment
NZ$1,009 per night
includes taxes & fees
2 Bed, 1.5 Bath Stunning Apartment, Central Andover Location
Terrace/patio
Exceptional
(159 reviews)

Charming private townhouse-style lodging, a block from Marblehead Harbor

Marblehead

8% off
NZ$3,339
for 7 nights, 1 home
NZ$477 per night
includes taxes & fees
Charming private townhouse-style lodging, a block from Marblehead Harbor
Dining
Exceptional
(50 reviews)

Samuel Tucker House - Downtown Luxury 2 Bedroom Condo

Marblehead

7% off
NZ$3,295
for 7 nights, 1 apartment
NZ$471 per night
includes taxes & fees
Samuel Tucker House - Downtown Luxury 2 Bedroom Condo
Property grounds
Exceptional
(18 reviews)

Waterfront 2 Bedroom Unit

Salem

17% off
NZ$4,018
for 7 nights, 1 apartment
NZ$574 per night
includes taxes & fees
Waterfront 2 Bedroom Unit
Private kitchen
Exceptional
(34 reviews)

Moody Salem Home Away From Home

Salem

7% off
NZ$2,381
for 7 nights, 1 home
NZ$340 per night
includes taxes & fees
Moody Salem Home Away From Home
Brand new open kitchen.
Exceptional
(54 reviews)

1880 updated Victorian 1st floor, water views

Salem

12% off
NZ$2,610
for 7 nights, 1 apartment
NZ$373 per night
includes taxes & fees
1880 updated Victorian 1st floor, water views
Living area
Exceptional
(20 reviews)

Hocus Pocus Season is here! Don’t miss it!

Salem

6% off
NZ$2,305
for 7 nights, 1 apartment
NZ$329 per night
includes taxes & fees
Hocus Pocus Season is here! Don’t miss it!
View from dining area into living area.
Exceptional
(15 reviews)

2-Bed Penthouse with Rooftop Deck in Old Town, Harbor Peeks and Parking

Marblehead

7% off
NZ$4,760
for 7 nights, 1 apartment
NZ$680 per night
includes taxes & fees
2-Bed Penthouse with Rooftop Deck in Old Town, Harbor Peeks and Parking
Property grounds
Exceptional
(54 reviews)

Fresh New Space, Walk to Salem Harbor, Historic

Salem

8% off
NZ$2,543
for 7 nights, 1 apartment
NZ$363 per night
includes taxes & fees
Fresh New Space, Walk to Salem Harbor, Historic
Living area
Exceptional
(181 reviews)

Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!

Salem

11% off
NZ$3,247
for 7 nights, 1 apartment
NZ$464 per night
includes taxes & fees
Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!
Room
Wonderful
(12 reviews)

Charming 2-bedroom apt in Beverly! Walking distance to the train - Enjoy Boston!

Beverly

12% off
NZ$2,988
for 7 nights, 1 apartment
NZ$427 per night
includes taxes & fees
Charming 2-bedroom apt in Beverly! Walking distance to the train - Enjoy Boston!
.
Exceptional
(71 reviews)

Family friendly home in historic Salem

Salem

8% off
NZ$7,207
for 7 nights, 1 apartment
NZ$1,030 per night
includes taxes & fees
Family friendly home in historic Salem
Interior
Exceptional
(59 reviews)

Beautiful Sunny Apartment in Salem

Salem

8% off
NZ$3,476
for 7 nights, 1 apartment
NZ$497 per night
includes taxes & fees
Beautiful Sunny Apartment in Salem
Living area
Exceptional
(42 reviews)

Lovely Downtown Beverly

Beverly

8% off
NZ$3,995
for 7 nights, 1 home
NZ$571 per night
includes taxes & fees
Lovely Downtown Beverly

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Take in the natural beauty of Middleton

The wildlife and parks create a pretty picture of Middleton. This city's restaurants, theme park and shopping draw many visitors. Fenway Park and Encore Boston Harbor are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Middleton

Are you hoping to find attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Middleton a one-of-a-kind holiday spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Encore Boston Harbor (14.1 mi / 22.7 km)
  • Water Park of New England (2.3 mi / 3.8 km)
  • Bewitched in Salem (8.1 mi / 13 km)
  • Tewksbury Country Club (9.6 mi / 15.5 km)
  • LEGO® Discovery Center Boston (14.2 mi / 22.9 km)
  • New England Aquarium (16.4 mi / 26.4 km)

Exploring the natural features in Middleton

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Middleton is a great place to spend some time outside. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (16.8 mi / 27 km)
  • Copley Square (17.2 mi / 27.7 km)
  • Glen Magna Farms (2.9 mi / 4.6 km)
  • Danvers Dog Park (3.1 mi / 5.1 km)
  • Salem Harbor (9.3 mi / 15 km)
  • Ipswich River (10.7 mi / 17.2 km)

Transport options to and around Middleton

Fly into Beverly, MA (BVY-Beverly Municipal), the closest airport, located 5.3 mi (8.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Lawrence, MA (LWM-Lawrence Municipal), which is 9.8 mi (15.8 km) away.

Frequently asked questions

What is the best area to stay in Middleton when booking a holiday rental?
When considering a holiday rental in Middleton, Massachusetts, a fantastic area to stay is near the town centre. This charming area offers a delightful mix of suburban tranquillity and easy access to local amenities. You'll find a variety of properties available, from cosy cottages to spacious family homes, making it suitable for different group sizes and preferences.One of the top attractions nearby is the beautiful Middleton Pond, which provides a serene setting for outdoor activities such as walking, picnicking, and birdwatching. Additionally, the town is conveniently located close to the Ipswich River, offering opportunities for kayaking and canoeing, great for those who enjoy spending time on the water.For dining and shopping, the local eateries and boutiques add to the charm of the area, ensuring you have a pleasant and fulfilling stay.
What is the most popular type of holiday rental accomodation in Middleton?
In Middleton, apartments are the most popular type of holiday rental, with several options available throughout the area. These apartments typically feature modern amenities such as fully equipped kitchens, spacious living areas, and comfortable bedrooms, making them suitable for both short and extended stays. Many are located in quiet residential neighbourhoods, providing a peaceful environment while still being within reach of local attractions and the natural beauty of the surrounding region.
Are there any remote work holiday rentals in Middleton?
In Middleton, Massachusetts, there are several remote work holiday rentals available, providing a suitable environment for those looking to balance work and leisure. Many of these properties come equipped with essential amenities such as reliable internet access through third-party services, allowing for seamless connectivity during your stay.Travellers can expect comfortable accommodations that often include dedicated workspaces, making it easier to focus on tasks while enjoying the charm of the area. Middleton is conveniently located near scenic parks and recreational areas, offering opportunities for outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Middleton?
In Middleton, popular rental amenities include WiFi, which is essential for staying connected during your visit. Many holiday rentals in the area offer this feature, ensuring guests can easily access the internet for work or leisure. Additionally, many properties provide comfortable living spaces, kitchens for self-catering, and outdoor areas for relaxation.
When is the best time to visit Middleton for a holiday rental?
The best time to visit Middleton for a holiday rental is during the peak season from July to September. This vibrant period draws families and outdoor enthusiasts, eager to enjoy the warm summer weather and the many local festivals that celebrate the area's rich culture and community spirit. With temperatures typically ranging from 20 to 30 degrees Celsius, it's an ideal time for outdoor activities, such as hiking in nearby parks or exploring the scenic beauty of the North Shore.July stands out as the most popular month, bustling with visitors who appreciate the lively option. It's the great time to take advantage of Middleton's numerous attractions, including its charming downtown shops and local dining options, all while soaking up the sun.For those seeking a more budget-friendly experience, consider visiting in December. While this month is quieter, it offers a unique charm with the festive decorations and holiday spirit, making it a delightful time for a peaceful getaway.Ultimately, your choice of when to visit Middleton will depend on whether you prefer the vibrant summer energy or the tranquil beauty of the winter season.
What are the top attractions in Middleton?
In Middleton, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local charm. One of the standout locations is the beautiful Middleton Pond, where guests can enjoy outdoor activities like fishing and kayaking while enjoying the scenic views. The nearby Harold Parker State Forest offers extensive walking and biking trails, superb for nature enthusiasts looking to explore the lush woodlands.For those interested in history, the town is home to several historic sites, including the Middleton Historical Society, where guests can learn about the local heritage. Additionally, the area boasts charming local shops and eateries that provide a taste of New England hospitality.
Are all fees included in the Middleton holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Middleton holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Middleton with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Middleton holiday homes?
You can find great discounts on holiday homes in Middleton on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Middleton holiday home booking on Bookabach?
To find Middleton holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Middleton?
A long-stay holiday home in Middleton is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Middleton holiday home?
Book your Middleton holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Middleton?
Prices for holiday homes in Middleton vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Middleton to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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