Search Vacation Homes in Middleton

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Middleton vacation homes

House (Plovers Nest) | Exterior
Plovers Nest

Vacation Home in Newburyport

3.0 star property
10.0 out of 10, Exceptional, (2)
"Clean and well cared for; high end finishes; small but adorable with beautiful views from upstairs bedroom. Good communication with owners. "
United States
Anat
Plovers Nest
Smart TV, fireplace
2BR Historic Marblehead Home+Minutes to Beach

Vacation Home in Marblehead

2.0 star property
10.0 out of 10, Exceptional, (18)
"Enjoyed our stay. "
United States
Mary D.
The price is AED 344
AED 1,274 total
includes taxes & fees
10 Dec - 11 Dec
2BR Historic Marblehead Home+Minutes to Beach
Smart TV, books
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill

Vacation Home in Rockport

2.0 star property
9.8 out of 10, Exceptional, (7)
"We had a great stay! Perfect location and a great setup for our family. Beautiful outdoor area and we were lucky with the weather! "
United States
Matt T.
The price is AED 360
AED 1,280 total
includes taxes & fees
10 Dec - 11 Dec
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill
Lake
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6

Vacation Home in Ipswich

9.4 out of 10, Exceptional, (70)
"Comfortable stay in a great location."
United States
Amanda A.
The price is AED 474
AED 963 total
includes taxes & fees
1 Jan - 2 January 2026
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 6
Interior
3BR3Bth Entire House/Steps to Downtown & TD Garden

Vacation Home in North End

10.0 out of 10, Exceptional, (2)
"Clean and bright throughout, host was great with timely responses to all inquiries. Maybe not the best for young children bc of the all the stairs (which are beautiful btw)."
United States
Margaret S.
The price is AED 948
AED 2,183 total
includes taxes & fees
15 Dec - 16 Dec
3BR3Bth Entire House/Steps to Downtown & TD Garden
Beach nearby, sun loungers
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Vacation Home in Rockport

2.0 star property
10.0 out of 10, Exceptional, (35)
"This is a great place to stay! It was super clean and comfy. I would go back! "
United States
Amanda C.
The price is AED 413
AED 1,356 total
includes taxes & fees
16 Dec - 17 Dec
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Terrace/patio
Gorgeous Beacon Hills Studio next to State house

Vacation Home in Beacon Hill

9.8 out of 10, Exceptional, (30)
"great room and better location "
United States
jonathan C.
The price is AED 731
AED 1,376 total
includes taxes & fees
30 Dec - 31 Dec
Gorgeous Beacon Hills Studio next to State house
Outdoor dining
Nothing Fancy Older Pet Friendly Home – near I-95

Vacation Home in Georgetown

9.0 out of 10, Wonderful, (2)
"Such a great place! Lots of room, beautiful backyard, and quiet. Perfect for relaxing after a day of exploring. We would love to stay again! "
United States
Megan H.
The price is AED 367
AED 1,079 total
includes taxes & fees
10 Dec - 11 Dec
Nothing Fancy Older Pet Friendly Home – near I-95
Fridge, microwave, oven, stovetop
LUXE 3BR Near Boston, Airport, and Beach!

Vacation Home in Revere

9.8 out of 10, Exceptional, (6)
"Very nice and comfortable place to stay in a very quiet neighborhood. Host was very caring and quick to respond. Two thumbs up👍👍"
Canada
Irma S.
The price is AED 342
AED 1,125 total
includes taxes & fees
14 Dec - 15 Dec
LUXE 3BR Near Boston, Airport, and Beach!
Property grounds
Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Vacation Home in Salem

2.0 star property
10.0 out of 10, Exceptional, (18)
"Stayed here with the family for a wedding and then stuck around a couple days to see the sights. Wonderful location since we were able to walk almost everywhere we wanted to go. "
United States
Nancy B.
The price is AED 552
AED 1,642 total
includes taxes & fees
15 Dec - 16 Dec
Entire 4BR 2 Bath Home l Minutes to Downtown Salem
TV
LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino

Vacation Home in East Somerville

10.0 out of 10, Exceptional, (2)
"Great stay and host was very responsive to any questions. "
United States
Matt R.
The price is AED 566
AED 1,489 total
includes taxes & fees
5 Jan - 6 January 2026
LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino
Fridge, microwave, oven, stovetop
Home w/firepit l Walk to Bearskin Neck+Beach

Vacation Home in Rockport

2.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful house, lots of places and nooks to sit and enjoy. Great ammenities, very cozy, well stocked. A short walk to the beach to enjoy sunrises..A short walk to city center, friendly people, great art scene. We loved our stay and would love to come again."
United States
gila
The price is AED 552
AED 1,773 total
includes taxes & fees
10 Dec - 11 Dec
Home w/firepit l Walk to Bearskin Neck+Beach
Interior
Rockport Pool House w/ Yard+Grill l 4BR/3BA l Park and Walk to Bearskin Neck!

Vacation Home in Rockport

2.0 star property
9.6 out of 10, Exceptional, (9)
"Great location to visit Bearskin Neck. Lovely neighborhood on a cul de sac, so no traffic.The home was spacious. Big kitchen, a separate dining room, tv room that comfortably sits 8 or play games with the family. Entire home was well kept. Beautiful pool, clean and seating outside for 8-10."
United States
Bradley S.
Rockport Pool House w/ Yard+Grill l 4BR/3BA l Park and Walk to Bearskin Neck!
Fridge, microwave, oven, stovetop
Historic 1686 Home Near Downtown l 5BR Retreat

Vacation Home in Beverly

2.0 star property
9.4 out of 10, Exceptional, (13)
"The house was perfect "
United States
Patrick J.
The price is AED 795
AED 2,320 total
includes taxes & fees
15 Dec - 16 Dec
Historic 1686 Home Near Downtown l 5BR Retreat
Exterior
✨Private Studio w/ Loft Center Historic Carlisle✨

Vacation Home in Carlisle

9.4 out of 10, Exceptional, (33)
"We had a great stay! The place was perfect for our weekend trip. We were able to hit all of the spots we planned, with the central location!"
United States
C Z.
The price is AED 364
AED 656 total
includes taxes & fees
14 Dec - 15 Dec
✨Private Studio w/ Loft Center Historic Carlisle✨
Fridge, microwave, oven, stovetop
Across From Beach | High-End Home | "The Nest"

Vacation Home in Newbury

10.0 out of 10, Exceptional, (13)
"Wolf appliances, top notch fixtures, comfortable bed, large deck. Such a comfortable place to stay"
United States
Stephanie R.
The price is AED 738
AED 1,735 total
includes taxes & fees
10 Dec - 11 Dec
Across From Beach | High-End Home | "The Nest"
Outdoor dining
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit

Vacation Home in Gloucester

9.6 out of 10, Exceptional, (10)
"We loved cooking on the antique stove and hanging out in the sun room. It was a cozy spot close to all the activities in Rockport."
United States
Allyson Y.
The price is AED 378
AED 1,317 total
includes taxes & fees
10 Dec - 11 Dec
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
Fridge, microwave, oven, stovetop
Moody Salem Home Away From Home

Vacation Home in Salem

9.8 out of 10, Exceptional, (21)
"The house was clean and perfect for my husband and i. The hosts was very accommodating and answerd right away when asked any questions. It really was a home away from home. Walking distance to everything in Salem. Would stay there again. "
United States
Brandy
The price is AED 298
AED 968 total
includes taxes & fees
14 Dec - 15 Dec
Moody Salem Home Away From Home
Fridge, dishwasher, cookware/dishes/utensils
PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino

Vacation Home in Everett

9.2 out of 10, Wonderful, (5)
"Barry was just the best. Great communication. Lovely home. Described just as listed maybe even nicer. We enjoyed our stay. Pretty close to everything. Thank you for sharing your home with us! "
United States
sarah J.
The price is AED 553
AED 1,083 total
includes taxes & fees
10 Dec - 11 Dec
PEACEFUL CHARM - Humble Luxury minutes from Boston, Beach & Casino
Fishing
Plovers Nest: Stay in the Heart of Newburyport During Yankee Homecoming Festivities!

Vacation Home in Newburyport

10.0 out of 10, Exceptional, (76)
"This was our second time here, and we LOVED it. Would highly recommend!"
United States
Nicole V.
The price is AED 481
AED 1,415 total
includes taxes & fees
18 Dec - 19 Dec
Plovers Nest: Stay in the Heart of Newburyport During Yankee Homecoming Festivities!
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

The Langham, Boston

The Langham, Boston

10/10 Excellent
"Lovely hotel, clean room, incredibly comfortable bed, great breakfast, kind staff. That's all I ask for. "
Robert 2-night trip
Posted 2 days ago
The Langham, Boston