A large, two-story house with a gabled roof, surrounded by lush green trees and a stone wall.

Middleton Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Middleton vacation rentals

Studio | Iron/ironing board, free WiFi

The Concord Hotel

The Concord Hotel
2.0 star property
South End
10.0 out of 10, Exceptional, (1 review)
"Overall had a great experience here. Took just a couple minutes texting the host to get the check in information that was to be emailed- but they sent it pretty quickly when I said it wasn't sent yet. I didn't need anything else from the host. It was clean and overall pretty nice! The stairs you take to get up to the room are pretty loud, so I woke up one time when other people got home to other rooms during my stay, but that was it! Overall good. I was there for a holiday weekend so the price...
United States
Jessica
$262 nightly
The price is $301
Jun 30 - Jul 1
Total with taxes and fees
The Concord Hotel
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (33 reviews)
"Charming room, fresh towels, clean!! I would stay here again."
United States
Mary
$270 nightly
The price is $310
Jun 30 - Jul 1
Total with taxes and fees
The Chester Hotel
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (396 reviews)
"Wonderful stay at this property. Location was excellent, and the host is very quick and responsive to answer any questions you may have."
United States
Jennifer
$153 nightly
The price is $176
Jun 30 - Jul 1
Total with taxes and fees
Temple Place Suites
Exterior

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

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.4 out of 10, Very Good, (23 reviews)
"Friendly hosts"
United States
Jan
$199 nightly
The price is $217
Jun 30 - Jul 1
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT
Exterior

Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
10.0 out of 10, Exceptional, (3 reviews)
"It was a great stay!"
United States
Adina S.
$194 nightly
The price is $250
Jul 5 - Jul 6
Total with taxes and fees
Light-filled Studio | Back Bay
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (296 reviews)
"Great location and well maintained"
United States
EDDIE
$154 nightly
The price is $177
Jun 29 - Jun 30
Total with taxes and fees
Premier Suites - Bay Village
Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down comforters

Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (6 reviews)
"The property was great, aside from very busy outside streets, which made it difficult to sleep, but was not the fault of the host."
United States
Nicholas
$237 nightly
The price is $272
Jun 30 - Jul 1
Total with taxes and fees
Symple Live
TV

Prime Central 1brm in North End Boston

Prime Central 1brm in North End Boston
North End
9.6 out of 10, Exceptional, (25 reviews)
"Excellent location, wonderful unit! "
United States
Mary M.
$366 nightly
The price is $421
Jul 2 - Jul 3
Total with taxes and fees
Prime Central 1brm in North End Boston
Interior

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.8 out of 10, Exceptional, (11 reviews)
"Great place to stay close to Boston. Lots of food choices in the immediate area. The space was clean, spacious and had a great old school charm. "
United States
Ashleigh K.
$208 nightly
The price is $228
Jul 6 - Jul 7
Total with taxes and fees
Enjoyable 2-bedroom lower level apartment in charming Lynn
TV

Dwtn Beverly! 5 Min to Salem!

Dwtn Beverly! 5 Min to Salem!
Beverly
9.0 out of 10, Wonderful, (18 reviews)
"Great location!!! Great rental, excellent host!!"
United States
Jennifer G.
$218 nightly
The price is $232
Jun 29 - Jun 30
Total with taxes and fees
Dwtn Beverly! 5 Min to Salem!
Exterior

Blissful South End Studio

Blissful South End Studio
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
$231 nightly
The price is $298
Jun 30 - Jul 1
Total with taxes and fees
Blissful South End Studio
Fridge, microwave, oven, stovetop

Luxury 1900's romantic retreat steps from the beach - King Suite!

Luxury 1900's romantic retreat steps from the beach - King Suite!
Gloucester
9.8 out of 10, Exceptional, (54 reviews)
"We enjoyed every bit of our stay."
United States
Kathy B.
$326 nightly
The price is $364
Jul 1 - Jul 2
Total with taxes and fees
Luxury 1900's romantic retreat steps from the beach - King Suite!
TV

Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
8.0 out of 10, Very Good, (1 review)
"Although we enjoyed the property, the pics were deceiving."
United States
Barry G.
$255 nightly
The price is $329
Jul 1 - Jul 2
Total with taxes and fees
Beautiful 1BR near Fenway Park + Kenmore!
Exterior

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very Good, (176 reviews)
"Room was clean and near the shops of Back Bay"
United States
Steven
$122 nightly
The price is $141
Jun 30 - Jul 1
Total with taxes and fees
Maverick Suites at 245 Newbury St
1 bedroom, desk, iron/ironing board, WiFi

Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.4 out of 10, Very Good, (21 reviews)
"Very easy check in, great location to walk to the ballet. Tons of great bars around"
United States
Keith
$201 nightly
The price is $236
Jun 30 - Jul 1
Total with taxes and fees
Perfect One Bedroom Stay In Downtown Boston!
Exterior

✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨
Carlisle
9.4 out of 10, Exceptional, (34 reviews)
"Wonderful stay"
United States
Brent H.
$155 nightly
The price is $163
Jun 29 - Jun 30
Total with taxes and fees
✨Private Studio w/ Loft Center Historic Carlisle✨
TV

Central Salem Retreat 2bd W/ parking

Central Salem Retreat 2bd W/ parking
Salem
9.0 out of 10, Wonderful, (17 reviews)
"It was very clean, a great location, and the host was super responsive and helpful!"
United States
Kristen N.
$286 nightly
The price is $290
Jul 7 - Jul 8
Total with taxes and fees
Central Salem Retreat 2bd W/ parking
Front of property

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (121 reviews)
"This was. A very nice, clean room. Plenty big enough for one or two people and great location, lots of dining and by the park"
United States
Rachel
$145 nightly
The price is $167
Jun 29 - Jun 30
Total with taxes and fees
Maverick Suites at 40 Temple St
Fridge, microwave, oven, stovetop

2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (25 reviews)
"Enjoyed our stay. "
United States
Mary D.
$359 nightly
The price is $401
Jun 29 - Jun 30
Total with taxes and fees
2BR Historic Marblehead Home+Minutes to Beach
1 bedroom, desk, iron/ironing board, WiFi

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
8.4 out of 10, Very Good, (6 reviews)
"Would stay again"
United States
mark p.
$195 nightly
The price is $229
Jun 30 - Jul 1
Total with taxes and fees
Studio Awaits Your Next Stay!
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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Good access and comfortable interior, including the nice coffee bar"
Spyridon 2-night trip
Posted less than an hour ago
Hyatt Regency Boston/Cambridge

Find out more about Middleton

Everything you need to know about Middleton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middleton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middleton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middleton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middleton. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middleton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middleton rentals

At Expedia, we put the best Middleton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middleton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middleton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middleton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.