50 Best Cape Ann Vacation rentals on Holiday Lettings - Apartments

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Cape Ann

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146 Vacation rentals

(26) Excellent 

23

Vacation cottage with golf nearby in Cape Ann

Cape Ann / Rockport

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Car not necessary
PERIWINKLE COTTAGE - truly a place to call "a home away from home". This 2-unit, townhouse cottage offers guests privacy and an updated seaside decor with today's modern amenities. (You can only reserve Unit #1 on this site). UNIT #1; --Unfortunately, we are NOT able …see more

from $125 / night

$875 / week

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from $125 / night

(8) Excellent 

46

Vacation apartment in Cape Ann

Cape Ann / Gloucester

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This place is a diamond in the rough - as one of my guests proclaimed. The view is spectacular! The apartment is inside a commercial marine building so it's right on top of the water, where the ships come in to unload lobsters and other catches. The apartment itself is …see more

from $110 / night

$893 - $1432 / week

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from $110 / night

22

Cottage rental in Cape Ann

Cape Ann / Gloucester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
Front row seats from every room and deck to view glorious evening sunsets over the Annisquam River and Ipswich Bay. Sunset Cottage is a charming 2 bedroom, 1 bath cottage on Gloucester’s Thurston Point that sits directly on the tidal Annisquam River and boasts unparalle …see more

from $383 / night

$1650 - $2448 / week

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from $383 / night

22

Vacation home in Cape Ann

Cape Ann / Rockport

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Ask about children
This spacious 5 BR vacation rental home is steps from Old Garden Beach as well as a short stroll into the seaside village of Rockport. Make this delightful and immaculate property your home base for your beach escape this summer. The main level of the home consists of …see more

from $800 / night

$4000 - $5000 / week

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from $800 / night

25

Gloucester Vacation apartment rental

Cape Ann / Gloucester

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Glouce …see more

from $583 / night

$2700 - $3650 / week

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from $583 / night

28

Cottage rental in Cape Ann

Cape Ann / Gloucester

7 12 Min stay varies

  • 7 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
Golden Sands is the quintessential turn of the century Gloucester beach "cottage." With views of Good Harbor Beach, the twin lighthouses of Rockport and the scenic Atlantic Ocean from its wrap around porch and decks, you will never want to leave this amazing beach hous …see more

from $1000 / night

$4975 - $7150 / week

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from $1000 / night

(9) Very Good 

7

Vacation cottage rental

Cape Ann / Rockport

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Car not necessary
Inquire Winter Rates Specials Just as sweet as icing on a cupcake - This downtowner located in a court yard makes a perfect getaway since you can stroll to the beach and to all the cultural and seafood eateries located within a stones throw of your front door. …see more

from $90 / night

$625 / week

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from $90 / night

(2) Excellent 

9

Vacation apartment in Gloucester

Cape Ann / Gloucester

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 1 mi
  • Air conditioning
On the peak of a hill on Cape Ann with spectacular panoramic, outside views of the beach,back shore, and even outer Boston Harbor. Secluded, but close to everything. Walk to the beach. Located between Bass Rocks and Brier Neck. Close to Rockport.Sleeps 2 -4. Bright, gr …see more

from $120 / night

$650 / week

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from $120 / night

29

Vacation cottage in Cape Ann

Cape Ann / Gloucester

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
This sweet and comfortable waterfront vacation rental cottage with spectacular sunset views over the Annisquam River offers a wonderful New England retreat. The main floor of the home consists of a charming open living and dining area, a small but well-equipped kitch …see more

from $440 / night

$1800 - $2283 / week

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from $440 / night

28

Vacation home in Gloucester

Cape Ann / Gloucester

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children
This comfortable recently renovated 3 BR vacation home is conveniently located a block away from Gloucester's scenic outer harbor. You'll love being just steps away from Gloucester's historic Stage Fort Park, once a landing place for pirates, now home to two public beac …see more

from $250 / night

$1250 - $1750 / week

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from $250 / night

21

Rockport Vacation home rental

Cape Ann / Rockport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This spacious and fully air conditioned vacation home boasts a lovely landscaped in-ground pool in a private, fenced-in yard. In the center of charming Rockport, the home is only two blocks from Old Garden Beach and Rockport harbor. A short stroll takes you to Bearskin …see more

from $733 / night

$3200 - $4692 / week

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from $733 / night

19

Cottage rental in Cape Ann

Cape Ann / Gloucester

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
Enjoy the views of the sparkling Annisquam River, lovely Wingaersheek Beach and the Annisqaum Yacht Club just across the river. You'll also be wowed by the incredible sunsets that await you every evening from this 3 bedroom/3.5 bath vacation rental home, which efficient …see more

from $440 / night

$2175 - $3000 / week

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from $440 / night

22

Vacation cottage in Gloucester

Cape Ann / Gloucester

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Enjoy a peaceful retreat in coastal New England by staying at this lovely Gloucester vacation rental cottage! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby beaches, this residence will surely become a place you love r …see more

from $209 / night

$1463 - $1813 / week

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from $209 / night

(10) Excellent 

25

Cape Ann Vacation home rental

Cape Ann / Gloucester

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Spacious 5 Bedroom Brick Colonial Home located on the Historic Stacey Boulevard with picturesque views of Gloucester's Harbor and the Atlantic Ocean. Look out at the stunning views of local schooners, the light houses, fishing vessels and feel the cool sea breeze that …see more

from $325 / night

$2200 - $2600 / week

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from $325 / night

17

Vacation home in Cape Ann

Cape Ann / Gloucester

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.32 mi
  • Child friendly
**There is a possibility that construction will ongoing near the property during the summer of 2016** Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms, two …see more

from $429 / night

$3250 / week

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Responds fast!
avg. 2 hours 23 minutes

from $429 / night

(1) Excellent 

14

Cape Ann Vacation b&b rental

Cape Ann / Rockport

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
Captain's Quarters,at Changing Tides Bed and Breakfast, features a queen-sized bed, two skylights and a shared bath, sleep well and look forward to a gourmet breakfast. Beaches, downtown shops and galleries are all within a short walk of our home. This room is located …see more

from $135 / night

$945 / week

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Responds fast!
avg. 2 hours 52 minutes

from $135 / night

21

Vacation home in Cape Ann

Cape Ann / Gloucester

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
This delightful 3 bedroom, 1.5 bath Queen Anne-style vacation rental home is bright and cheery and just waiting for you! Enter the house into the kitchen from the verdant and sizable back yard (or choose one of the other 2 doors). The sunny kitchen has plenty of stor …see more

from $320 / night

$1250 - $1815 / week

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from $320 / night

21

Vacation home in Cape Ann

Cape Ann / Rockport

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Pet friendly
If you are looking for a beach house, this is it. Walk to Long or Cape Hedge beaches in 5 minutes or just relax at this fun vacation rental home and enjoy the water views from one of two decks. Sea Vagabond House is actually two houses in one; the original cottage downs …see more

from $235 / night

$1175 - $2400 / week

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from $235 / night

11

Vacation home in Cape Ann

Cape Ann / Rockport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Quaint cozy pre-Revolutionary house with priceless view of picturesque Rockport village and Atlantic Ocean. Located on quiet dead-end lane next to tranquil pond and small town park. Two-minute walk to beach and town's attractive Main street with shops, art galleries and …see more

from $143 / night

$800 - $1200 / week

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from $143 / night

(5) Excellent 

21

Vacation apartment in Cape Ann

Cape Ann / Rockport

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Built in 1900, this classic New England beach house is located in the Headlands neighborhood in Rockport, Massachusetts. Steps away is the charming Old Garden Beach, secluded enough to remain a hidden jewel of Rockport. Also a short walk away is the Headlands, providing …see more

from $199 / night

$999 - $2494 / week

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from $199 / night

(5) Excellent 

15

Vacation b&b in Rockport

Cape Ann / Rockport

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
BOOKING ACCEPTED NOW FOR SUMMER 2016!!. DEDICATED OFF-STREET PARKING FOR ONE CAR. BEST LOCATION IN ROCKPORT steps away from everything! Ground floor studio boasts comfortable and clean efficiency with AC, cable TV and microwave kitchenette, private entrance, private b …see more

from $125 / night

$950 / week

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Responds fast!
avg. 2 hours 29 minutes

from $125 / night

21

Vacation home in Cape Ann

Cape Ann / Gloucester

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
New in 2017! Enjoy the ambiance of Victorian Gloucester with all the amenities of the 21st century from this classic period vacation rental home, which is tastefully decorated with the traveler in mind. Enter the house through the front door and enjoy two parlors--one w …see more

from $520 / night

$2600 - $3458 / week

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from $520 / night

30

Home rental in Gloucester

Cape Ann / Gloucester

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Ask about children
Enjoy the best sunsets on the East Coast from this classic riverfront Victorian summer retreat. Annisquam Singing Pines is situated on over an acre of waterfront land and has lovely gathering spaces both inside and out. It was built as an impressive yet casual vacation …see more

from $700 / night

$3500 - $4600 / week

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from $700 / night

11

Cape Ann Vacation studio rental

Cape Ann / Gloucester

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
Perfect for 1 or 2 guests looking for an affordable summer get-away in beautiful location. The studio can also accommodate an infant in a pack-n-play or porta-crib, who is not yet walking. Walk to Good Harbor Beach and scenic Back Shore. We call your home away from hom …see more

from $135 / night

$875 / week

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Responds fast!
avg. 2 hours 44 minutes

from $135 / night

37

Home rental in Cape Ann

Cape Ann / Gloucester

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Pet friendly
A tastefully renovated vacation home, Victorian House on Rocky Neck (Gloucester’s fabled artist colony) has three bedrooms and a gorgeous front porch overlooking the water. From the porch, step into the home’s front hall and formal living room, complete with a custom de …see more

from $467 / night

$2100 - $2958 / week

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from $467 / night

18

Vacation apartment with golf nearby in Rockport

Cape Ann / Rockport

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
The Seaward offers a spectacular setting and charming accommodations. Loblolly Cove, offers accommodations for up to 4 people. One bedroom has a queen sized bed, while the rather spacious living room has accommodations for two more. At Loblolly Cove, you will enjoy a …see more

from $179 / night

$1250 / week

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Responds fast!
avg. 1 hour 9 minutes

from $179 / night

20

Home rental in Cape Ann

Cape Ann / Gloucester

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Pet friendly
This large, comfortable family-oriented vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities. On the gro …see more

from $538 / night

$2600 - $3622 / week

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from $538 / night

29

Home accommodation in Cape Ann

Cape Ann / Essex

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
Available for rentals year round, Clamshell Landing is perfect for family vacations, family reunions, wedding accommodations, corporate outings or other events. This one-of-a-kind vacation rental home is perfect for sports enthusiasts or nature lovers and is complete wi …see more

from $1400 / night

$6600 - $8800 / week

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from $1400 / night

(6) Excellent 

24

Cape Ann Vacation apartment rental

Cape Ann / Rockport

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
The Mariner is a custom-furnished, luxury apartment with a panoramic harbor view and providing all the amenities and comfort that one may need to enjoy time in Rockport, Massachusetts. The Mariner, a 2nd floor apartment, is located at 35 Bearskin Neck. The fro …see more

from $199 / night

$999 - $2095 / week

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from $199 / night

16

Cape Ann Vacation condo rental

Cape Ann / Manchester-by-the-Sea

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Completely renovated 2+ bedroom, 1.25 bath. Second floor unit. Spacious designer kitchen w/ stainless steel appliances. Large Living room and wonderful master bedroom suite. Close to town center, commuter rail, and Singing Beach. 4 minute drive to Singing beach, 20 minu …see more

from $250 / night

$1600 - $1845 / week

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Responds fast!
avg. 2 hours 41 minutes

from $250 / night

(3) Very Good 

26

Vacation apartment in Cape Ann

Cape Ann / Gloucester

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Private garden
UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a ve …see more

from $135 / night

$851 - $1140 / week

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from $135 / night

37

Vacation home in Cape Ann

Cape Ann / Gloucester

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
This bright and open contemporary vacation rental home was custom-designed and built by the architect owner. The care and skill is reflected in the soaring ceilings, multitudes of windows and skylights, and warm pine floors, all of which bring the outside in -- yet all …see more

from $550 / night

$2500 - $3500 / week

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from $550 / night

26

Home rental in Rockport

Cape Ann / Rockport

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
This lovely 3 bedroom vacation home is appointed with high end appliances, finishes and furnishings while remaining very comfortable and accommodating inside and out. The house is located in the sought-after Marmion Way location which offers the ultimate Rockport experi …see more

from $567 / night

$2625 - $3570 / week

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from $567 / night

38

Vacation home in Gloucester

Cape Ann / Gloucester

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Air conditioning
This spacious and gracious vacation rental home offers incredible versatility to suit your specific vacation needs. The house can accommodate just your family or your extended group of up to 16, making it the perfect getaway for family reunions or vacations with friends …see more

from $960 / night

$4800 - $6732 / week

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from $960 / night

40

Vacation home in Cape Ann

Cape Ann / Gloucester

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Pet friendly
Located above the western shore of Gloucester’s historic harbor and lovingly renovated in 2011, this beautiful and spacious five bedroom Victorian vacation rental home has been in the same family since the 1880's. This gracious home gives hints to a bygone era while …see more

from $470 / night

$2350 - $3053 / week

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from $470 / night

24

Vacation home rental

Cape Ann / Rockport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
This immaculate vacation rental home is the perfect launching place for your Rockport summer adventure. Beachcomber has many large and comfortable gathering places, such as the custom kitchen, living room and separate family room. Equipped for fun, the home offers an el …see more

from $608 / night

$2725 - $3712 / week

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from $608 / night

(16) Excellent 

26

Cottage rental in Gloucester

Cape Ann / Gloucester

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Suitable for children age 5+
Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. Open living space - large living room with sliding door onto large pri …see more

from $250 / night

$1600 - $1960 / week

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Responds fast!
avg. 3 hours 32 minutes

from $250 / night

33

Vacation home in Cape Ann

Cape Ann / Gloucester

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Direct waterfront on picturesque Goose Cove, this immaculate vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat- …see more

from $450 / night

$2250 - $3050 / week

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from $450 / night

(4) Excellent 

17

Vacation home in Cape Ann

Cape Ann / Rockport

4 7 2 nights min

  • 4 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
Sitting directly on picturesque Long Beach, this is the perfect spot for a romantic get-away or a family retreat. With decks in the front and back of the house, sun-chasers and shade-seekers alike will be pleased at any time of day. The cottage is sunny and open with a …see more

from $400 / night

$3500 / week

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from $400 / night

1