Middleton Vacation Rentals

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Our top choices for Middleton vacation rentals

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Salem
9.6 out of 10, Exceptional, (151 reviews)
"It was nice to rent a place for just one night. Great place. Spacious and clean. "
United States
Sue J.
The price is CA $252
CA $584 total
includes taxes & fees
May 20 - May 21
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.4 out of 10, Very good, (30 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is CA $279
CA $494 total
includes taxes & fees
May 19 - May 20
The Chester Hotel

3BR3Bth Entire House/Steps to Downtown & TD Garden

3BR3Bth Entire House/Steps to Downtown & TD Garden
North End
10.0 out of 10, Exceptional, (10 reviews)
"This place is so cool! Was incredibly clean, updated and offered all the amenities you need for a weekend get away. The location is wonderful as well with lots of markets, bakeries and restaurants all within walking distance. This is a must stay! "
United States
mary j.
The price is CA $222
CA $651 total
includes taxes & fees
May 26 - May 27
3BR3Bth Entire House/Steps to Downtown & TD Garden

Primo North End Studio

Primo North End Studio
North End
9.2 out of 10, Wonderful, (14 reviews)
"Great place, amazing location!"
United States
Christopher W.
The price is CA $267
CA $558 total
includes taxes & fees
May 18 - May 19
Primo North End Studio

North End Entire House

North End Entire House
North End
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful home in the heart of the north end. We had a wonderful stay!"
United States
Kerry y.
The price is CA $222
CA $651 total
includes taxes & fees
May 26 - May 27
North End Entire House

Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6

Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6
Ipswich
9.4 out of 10, Exceptional, (70 reviews)
"Comfortable stay in a great location."
United States
Amanda A.
The price is CA $171
CA $353 total
includes taxes & fees
May 24 - May 25
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6

Ideal North End 1brm Central To Everything

Ideal North End 1brm Central To Everything
North End
9.6 out of 10, Exceptional, (41 reviews)
"Great well appointed place, close to everything Boston has to offer."
United States
Robert M.
Ideal North End 1brm Central To Everything

Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.0 out of 10, Very good, (14 reviews)
"Great location, check in and check out was easy. Clean space. Great value "
United States
David
The price is CA $178
CA $361 total
includes taxes & fees
May 19 - May 20
Free Parking at 1 Bed Basement Apt, Near BU & MIT

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
9.2 out of 10, Wonderful, (5 reviews)
"Would stay again"
United States
mark p.
The price is CA $215
CA $392 total
includes taxes & fees
Jun 10 - Jun 11
Studio Awaits Your Next Stay!

The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (5 reviews)
"The host was really accessible and easy to communicate with. We had all the info we needed for an easy check-in. The house was exceptionally clean and quiet. "
United States
Chris K.
The price is CA $306
CA $390 total
includes taxes & fees
May 13 - May 14
The Essex of Gloucester

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.6 out of 10, Excellent, (10 reviews)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
The price is CA $189
CA $434 total
includes taxes & fees
May 18 - May 19
Stylish Back Bay Retreat, Steps from Prudential

Blissful South End Studio

Blissful South End Studio
Back Bay
9.4 out of 10, Exceptional, (3 reviews)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
The price is CA $137
CA $383 total
includes taxes & fees
May 18 - May 19
Blissful South End Studio

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
Rockport
10.0 out of 10, Exceptional, (35 reviews)
"Great location and the host is very responsive. "
United States
Heather P.
The price is CA $482
CA $969 total
includes taxes & fees
May 14 - May 15
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.6 out of 10, Excellent, (18 reviews)
"Came to Boston to take a few college tours and this was a pretty central location. This property was also very close to several other places we were hoping to see while in town. Communication was great and check in was seamless. The property was clean and perfect for our stay. "
United States
elena d.
The price is CA $228
CA $413 total
includes taxes & fees
May 20 - May 21
Perfect One Bedroom Stay In Downtown Boston!

Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
10.0 out of 10, Exceptional, (26 reviews)
"Great property to stay with proximity to everything you need, and a safe neighborhood to walk all times of the day. The hosts were very communicative and quick to respond to any questions I had. The apartment itself was spacious and had a nice kitchen to prepare meals. I would recommend to all considering a stay in East Boston!"
United States
Jordan
The price is CA $239
CA $485 total
includes taxes & fees
Jun 1 - Jun 2
Bright 2BR by Boston Waterfront

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking
Beverly
9.2 out of 10, Wonderful, (24 reviews)
"Cheerful decor, well-equipped kitchen, and clean. Good location in walking distance to restaurants. However, there was a musty smell throughout the building and rooms. "
United States
Julia
The price is CA $123
CA $416 total
includes taxes & fees
May 13 - May 14
Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
8.0 out of 10, Very good, (12 reviews)
"Was clean and the location was perfect for my stay. "
United States
Laurie F.
The price is CA $212
CA $500 total
includes taxes & fees
May 17 - May 18
Cozy Studio Steps from Boston Common and Theaters

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (113 reviews)
"A phenomenal stay at maverick suites! The location was fantastic, the room was spotless and cozy, and the check-in/out process was a breeze. I’d happily stay here again and recommend to anyone taking a trip to Boston!"
United States
Kendra
The price is CA $299
CA $469 total
includes taxes & fees
May 24 - May 25
Maverick Suites at 40 Temple St

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very good, (41 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
The price is CA $233
CA $431 total
includes taxes & fees
May 26 - May 27
On River/Harvard Sq. two blocks

Gorgeous Beacon Hills Studio next to State house

Gorgeous Beacon Hills Studio next to State house
Beacon Hill
9.8 out of 10, Exceptional, (33 reviews)
"We had a great stay and host was welcoming and responsive. Thanks!"
United States
Eric M.
The price is CA $286
CA $538 total
includes taxes & fees
May 31 - Jun 1
Gorgeous Beacon Hills Studio next to State house
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middleton Hotel Reviews

Find out more about Middleton

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middleton. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Middleton?

Yes, we give you a choice of vacation rentals in Middleton near Water Park of New England, or you can go with a secluded option if you'd like a relaxing place to stay. Middleton is known for its restaurants and theme park. Make sure you have time to check out the shopping and parks during your trip.

What are some of the best vacation home rentals in Middleton?

Centrally located in the heart of Boston near T: You might want to consider this vacation home rental near Middleton, which has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Middleton?

Boxford State Forest and Ipswich River are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Water Park of New England. In the larger area, you’ll find popular places like Fenway Park and Encore Boston Harbor.

What’s a vacation rental in Middleton like?

Vacation rentals are private properties you can book for several days or longer in Middleton. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family gatherings.