Search Vacation Homes in Gloucester
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Our top choices for Gloucester vacation homes
$164 nightly
The price is $183
Dec 24 - Dec 25
Total with taxes and fees
Vacation Home in Gloucester
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit9.8 out of 10, Exceptional, (11)
"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."
Allyson Y.
$343 nightly
The price is $383
Jan 6 - Jan 7, 2026
Total with taxes and fees
Vacation Home in Ipswich
Cozy and beatifull 2br in New England . 5 min drive to the beach /sleeps 69.4 out of 10, Exceptional, (70)
"Comfortable stay in a great location."
Amanda A.
$205 nightly
The price is $225
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Home in Marblehead
2BR Historic Marblehead Home+Minutes to Beach10.0 out of 10, Exceptional, (18)
"Enjoyed our stay. "
Mary D.
$353 nightly
The price is $395
Dec 29 - Dec 30
Total with taxes and fees
Vacation Home in Newbury
The Nest • Luxury Monthly Stay • Across from Beach10.0 out of 10, Exceptional, (13)
"Very nice and comfortable stayHad everything we neededGreat location Could use some better beach chairsOnly had one good one."
Joseph W.
$388 nightly
The price is $410
Jan 7 - Jan 8, 2026
Total with taxes and fees
Vacation Home in Rockport
The Ladybug • 2BR Cottage Steps 2 Bearskin Neck • 2 Parking Spaces, Patio, Grill9.8 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! "
Matt T.
$348 nightly
The price is $389
Jan 12 - Jan 13, 2026
Total with taxes and fees
Vacation Home in Rockport
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed10.0 out of 10, Exceptional, (13)
"Cozy house in great location. We would definitely stay here again. "
John D.
$332 nightly
The price is $371
Dec 28 - Dec 29
Total with taxes and fees
Vacation Home in Rockport
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!10.0 out of 10, Exceptional, (35)
"Everything about our stay was perfect ! The house, its location to the beaches, town and the idyllic Millbrook Meadow Park. The check in was seamless, the house was very clean and had everything we needed. We are definitely going back! "
Tammi M.
$365 nightly
The price is $407
Jan 1 - Jan 2, 2026
Total with taxes and fees
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.
Top Gloucester Hotel Reviews
DoubleTree by Hilton Boston North Shore
10/10 Excellent
Find out more about Gloucester
Gloucester Vacation Homes information
Number of reviews | 312 |
|---|---|
Accommodation | 537 Vacation Homes |
Lowest Price | $183 |
Highest Price | $752 |
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- Sargent House Museum
- Gloucester Unitarian Universalist Church
- Cape Ann Historical Museum
- Capt Bill & Sons Whale Watch
- Maritime Gloucester
- Fishermen's Memorial Monument
- Schooner Adventure
- Rocky Neck Art Colony
- Half Moon Beach
- Stage Fort Park
- Good Harbor Beach
- Hammond Castle
- Niles Beach
- Dogtown
- Ravenswood Park
- Eastern Point Lighthouse
- Wingaersheek Beach
- Long Beach
- North Shore Vacations
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