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218 houses
One Bedroom Loft Apartment B at Cedar Hill Farm B & B
Cape Ann / Essex
1 4 2 nights min
- 1 bedroom
- sleeps 4
- 2 nights min
- Child Friendly
- Air conditioning
- Pet Friendly
Map
Price per night from
$201
Price per night from
$201
40% off regular rate: Wonderful 4 Bedroom, 2 Full Bath Restored 1917 Home
Cape Ann / Manchester-by-the-Sea
4 7 5 nights min
- 4 bedrooms
- sleeps 7
- 5 nights min
- Child Friendly
Map
Price per night from
$457
Price per night from
$457
Waterfront 2 Bedroom !
Cape Ann / Gloucester
2 4 min stay varies
- 2 bedrooms
- sleeps 4
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 2 mi
- Child Friendly
Map
Price per night from
$184
Price per night from
$184
The Rockporter: Enjoy beautiful views of Pigeon Cove Harbor.
Cape Ann / Rockport
4 7 3 nights min
- 4 bedrooms
- sleeps 7
- 3 nights min
- Ask about children
Map
Price per night from
$513
Price per night from
$513
The Friendship Room at Cedar Hill Farm B & B
Cape Ann / Essex
1 3 2 nights min
- 1 bedroom
- sleeps 3
- 2 nights min
- Child Friendly
- Air conditioning
- Private garden
Map
Price per night from
$172
Price per night from
$172
Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.
Cape Ann / Gloucester
3 6 3 nights min
- 3 bedrooms
- sleeps 6
- 3 nights min
- Ask about children
Map
Price per night from
$328
Price per night from
$328
Golden Sands at Good Harbor: Across the street from the beach
Cape Ann / Gloucester
7 12 min stay varies
- 7 bedrooms
- sleeps 12
- min stay varies
- Ask about children
Map
Price per night from
$868
Price per night from
$868
Family Friendly Apartment, Short Walk to Beach/Downtown, Parking, WiFi, Grill
Cape Ann / Rockport
2 7 2 nights min
- 2 bedrooms
- sleeps 7
- 2 nights min
- Beach / lakeside relaxation
- Nearest beach 0.3 mi
- Child Friendly
Map
Price per night from
$228
Price per night from
$228
Beautiful First Floor 2 BR Condo in Manchester
Cape Ann / Manchester-by-the-Sea
2 4 7 nights min
- 2 bedrooms
- sleeps 4
- 7 nights min
- Child Friendly
- Air conditioning
- Pet Friendly
Map
Price per night from
$245
Price per night from
$245
Beachcomber Suite
Cape Ann / Rockport
1 2 2 nights min
- 1 bedroom
- sleeps 2
- 2 nights min
- Car not necessary
- Air conditioning
- Private garden
Map
Price per night from
$201
Responds fast!
avg. 33 minutes
Price per night from
$201
Back Beach
Cape Ann / Rockport
4 8 7 nights min
- 4 bedrooms
- sleeps 8
- 7 nights min
- Child Friendly
- Air conditioning
- Ask about pets
Map
Price per night from
$491
Responds fast!
avg. 1 hour 6 minutes
Price per night from
$491
Second Floor: 2+ Bedroom, 1.25 Bath
Cape Ann / Manchester-by-the-Sea
3 5 4 nights min
- 3 bedrooms
- sleeps 5
- 4 nights min
- Child Friendly
Map
Price per night from
$287
Price per night from
$287
GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN
Cape Ann / Rockport
2 3 7 nights min
- 2 bedrooms
- sleeps 3
- 7 nights min
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Map
Price per night from
$245
Responds fast!
avg. 37 minutes
Price per night from
$245
18th Century Cottage with attached guest suite
Cape Ann / Rockport
2 6 7 nights min
- 2 bedrooms
- sleeps 6
- 7 nights min
- Child Friendly
- Ask about pets
Map
Price per night from
$213
Price per night from
$213
Oceans Views And Minutes Walk To Beach
Cape Ann / Rockport
4 8 3 nights min
- 4 bedrooms
- sleeps 8
- 3 nights min
- Child Friendly
Map
Price per night from
$327
Price per night from
$327
At the Footbridge entrance to Good Harbor Beach
Cape Ann / Gloucester
6 12 7 nights min
- 6 bedrooms
- sleeps 12
- 7 nights min
- Nearest beach 0 mi
- Child Friendly
- Private garden
Map
Price per night from
$653
Price per night from
$653
Granite Cottage: Charming cottage in Rockport with private deck and views
Cape Ann / Rockport
1 4 3 nights min
- 1 bedroom
- sleeps 4
- 3 nights min
- Ask about children
- Pet Friendly
Map
Price per night from
$253
Price per night from
$253
Bohemia RETREAT Studio
Cape Ann / Gloucester
1 3 3 nights min
- 1 bedroom
- sleeps 3
- 3 nights min
- Beach / lakeside relaxation
- Nearest beach 2 mi
- Private garden
Map
Price per night from
$132
Responds fast!
avg. 2 hours 16 minutes
Price per night from
$132
Poolside Summers: Swim in the private in-ground pool or walk to the beach
Cape Ann / Rockport
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Map
Price per night from
$487
Price per night from
$487
Diamond in the Sky: Upscale townhouse near Good Harbor Beach.
Cape Ann / Gloucester
3 7 3 nights min
- 3 bedrooms
- sleeps 7
- 3 nights min
- Ask about children
- Air conditioning
Map
Price per night from
$588
Price per night from
$588
Inviting apartment with harbor views, fireplace, patio, & gas grill!
Cape Ann / Gloucester
1 4 min stay varies
- 1 bedroom
- sleeps 4
- min stay varies
- Child Friendly
- Car not necessary
- Air conditioning
Map
Price per night from
$196
Responds fast!
avg. 2 hours 57 minutes
Price per night from
$196
NEW LISTING! Quaint getaway w/ kitchen & lush yard - near beach & town, dogs OK!
Cape Ann / Rockport
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Child Friendly
- Car not necessary
- Air conditioning
Map
Price per night from
$113
Responds fast!
avg. 2 hours 24 minutes
Price per night from
$113
Lovely 'Blue Heron Cottage' on Annisquam River!
Cape Ann / Gloucester
3 6 3 nights min
- 3 bedrooms
- sleeps 6
- 3 nights min
- Child Friendly
- Air conditioning
Map
Price per night from
$228
Responds fast!
avg. 33 minutes
Price per night from
$228
Waterfront Woodsy 3BR Cottage
Cape Ann / Gloucester
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Nearest beach 2 mi
- Child Friendly
- Pet Friendly
Map
Price per night from
$213
Price per night from
$213
North Seas Cottage: Water views in serene Pigeon Cove
Cape Ann / Rockport
2 4 min stay varies
- 2 bedrooms
- sleeps 4
- min stay varies
- Ask about children
- Pet Friendly
Map
Price per night from
$279
Price per night from
$279
Renovated 19th century home in pastoral setting
Cape Ann / Essex
2 6 3 nights min
- 2 bedrooms
- sleeps 6
- 3 nights min
- Ask about children
Map
Price per night from
$179
Price per night from
$179
Fabulous Waterfront 2 Bedroom - Boat dock option
Cape Ann / Gloucester
2 4 30 nights min
- 2 bedrooms
- sleeps 4
- 30 nights min
- Ask about pets
Map
Price per night from
$77
Price per night from
$77
Stunning Views - Spacious Home
Cape Ann / Gloucester
3 8 7 nights min
- 3 bedrooms
- sleeps 8
- 7 nights min
- Beach / lakeside relaxation
- Nearest beach 0.8 mi
Map
Price per night from
$573
Price per night from
$573
Captain Quarters
Cape Ann / Rockport
1 2 2 nights min
- 1 bedroom
- sleeps 2
- 2 nights min
- Air conditioning
Map
Price per night from
$184
Responds fast!
avg. 33 minutes
Price per night from
$184
Vintage Home directly on the Annisquam River
Cape Ann / Gloucester
6 12 4 nights min
- 6 bedrooms
- sleeps 12
- 4 nights min
- Beach / lakeside relaxation
- Ask about pets
Map
Price per night from
$360
Price per night from
$360
GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM
Cape Ann / Rockport
2 4 min stay varies
- 2 bedrooms
- sleeps 4
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 0.5 mi
- Child Friendly
Map
Price per night from
$216
Responds fast!
avg. 37 minutes
Price per night from
$216
Water's Edge: Direct waterfront on picturesque Goose Cove with dock
Cape Ann / Gloucester
3 8 3 nights min
- 3 bedrooms
- sleeps 8
- 3 nights min
- Ask about children
- Air conditioning
- Pet Friendly
Map
Price per night from
$453
Price per night from
$453
Cool Cove: Wingaersheek Beach plus your own private beach & all those views!
Cape Ann / Gloucester
4 8 3 nights min
- 4 bedrooms
- sleeps 8
- 3 nights min
- Ask about children
Map
Price per night from
$1,513
Price per night from
$1,513
Coolest House in Rockport: Newly Renovated Home Overlooking Pigeon Cove Floor 1
Cape Ann / Rockport
3 6 7 nights min
- 3 bedrooms
- sleeps 6
- 7 nights min
- Child Friendly
Map
Price per night from
$372
Price per night from
$372
Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town
Cape Ann / Gloucester
2 5 min stay varies
- 2 bedrooms
- sleeps 5
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 1 mi
- Child Friendly
Map
Price per night from
$138
Price per night from
$138
Happy Days Cottage: Charming Folly Cove house with waterfront deck
Cape Ann / Rockport
4 7 3 nights min
- 4 bedrooms
- sleeps 7
- 3 nights min
- Ask about children
- Pet Friendly
Map
Price per night from
$313
Price per night from
$313
Waterfront Vacation House w/ Dock
Cape Ann / Gloucester
2 4 min stay varies
- 2 bedrooms
- sleeps 4
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 2 mi
- Child Friendly
Map
Price per night from
$343
Responds fast!
avg. 1 hour 26 minutes
Price per night from
$343
Wonson Cove House: Rocky Neck, Eastern Point and Beaches
Cape Ann / Gloucester
4 10 min stay varies
- 4 bedrooms
- sleeps 10
- min stay varies
- Ask about children
- Pet Friendly
Map
Price per night from
$442
Price per night from
$442
About Cape Ann
Cape Ann, Massachusetts
This rocky cape in Northeastern Massachusetts lies around 30 miles northeast of the city of Boston. Home to the historic port of Gloucester and pretty towns and villages including Rockport, Essex and Manchester-by-the-Sea, you’re sure to find your perfect seaside vacation property in Cape Ann with FlipKey.
About Cape Ann, Massachusetts
Cape Ann has a rich history, and Gloucester is one of the oldest towns in New England, founded in 1623. The town’s economy has relied on fishing for over 400 years, and wherever you go on the Cape, you’ll see fishing boats and creels – the seafood here is as fresh as it comes!
With its gorgeous, white sandy beaches, watersports, fishing and whale watching, a vacation on Cape Ann has something to offer everyone, from families to couples looking for a romantic retreat away from the hustle and bustle of Boston.
While you’re here, don’t miss out on a trip to Essex, the Home of the Fried Clam. Dipped in milk and flour, deep-fried and served with tartar sauce, these are a local specialty you simply have to try!
What to do in Cape Ann, Massachusetts
Spend your days relaxing on one of Cape Ann’s beautiful beaches. The soft white sands of Good Harbor ensure it’s a popular choice, whilst Front Beach (Rockport) is great for swimming and Singing Beach (Manchester-by-the-Sea) is a hidden gem!
Explore the historic town of Gloucester, home to America’s oldest seaport. Take a self-guided tour of the Gloucester Harbor Walk with its 42 story markers highlighting local history and culture, or visit one of the five lighthouses dotted along the coastline.
Visit the Shipbuilding Museum in Essex for a fascinating insight into the shipbuilding industry that once put this town on the map, or shop for antiques in the town center. Or head for Manchester-by-the-Sea, when the Festival by the Sea takes place every July. This colorful celebration of local art, culture, music and food is fun for the whole family.
Top travel tips for Cape Ann
If you’re flying to Cape Ann, the nearest airport is Boston Logan International, just 42 miles from the center of Gloucester.
Come in the summer months if you want to enjoy whale watching tours. Cape Ann is located midway between two whale feeding grounds where you can also spot dolphins and sea birds.
With average temperatures of 75 degrees Fahrenheit in July and August, summer is the best time to visit, although spring in Cape Ann is also quite warm and sunny.
With white sandy beaches, a rich seafaring history and some of the freshest seafood around, a vacation to Cape Ann can be a relaxing or activity-packed as you want it to be. Why not browse FlipKey’s range of vacation rentals for your perfect property in Rockport, Gloucester or Essex today?
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