50 Best Gloucester Apartments on Holiday Lettings - Vacation rentals

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66 Vacation rentals

20

Gloucester Vacation apartment rental

Cape Ann / Gloucester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both …see more

from $220 / night

$1050 - $1632 / week

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from $220 / night

(8) Excellent 

46

Vacation apartment in Gloucester

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

(10) Excellent 

25

Gloucester 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

(3) Very Good 

26

Vacation apartment in Gloucester

Cape Ann / Gloucester

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 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 $115 / night

$805 / week

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from $115 / night

(1) Excellent 

24

Vacation cottage in Gloucester

Cape Ann / Gloucester

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
Enjoy a peaceful retreat in coastal New England by staying at this lovely 3-bedroom, 1-bathroom Gloucester vacation rental cottage, which sleeps 6! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby beaches, this residence …see more

from $209 / night

$1463 - $1813 / week

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from $209 / night

21

Vacation home in Gloucester

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

11

Vacation apartment in Gloucester

Cape Ann / Gloucester

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask about children
This perfectly-located vacation rental is a delightful ground floor apartment (in a two-unit building), right at Good Harbor Beach. With one bedroom and sleeping space for 3, this beach house is the perfect arrangement for couples and small families. Just step out the …see more

from $230 / night

$1300 - $1400 / week

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from $230 / night

22

Cottage rental in Gloucester

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

$1651 - $2448 / week

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from $383 / night

20

Home rental in Gloucester

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 - $3621 / week

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from $538 / night

28

Vacation home in Gloucester

Cape Ann / Gloucester

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Ideally situated between two of Cape Ann's most beautiful beaches, this immaculate and recently renovated vacation rental home is a mere 3-minute walk to Long Beach and an 8-minute walk to Good Harbor Beach. The home has a single level and an open floor plan that offers …see more

from $408 / night

$1750 - $2755 / week

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from $408 / night

37

Home rental in Gloucester

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

(2) Very Good 

12

Home rental in Gloucester

Cape Ann / Gloucester

6 12 4 nights min

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min
  • Beach/lakeside relaxation
  • Ask about pets
This six bedroom comfortable house has a large full equipped kitchen with two seating areas. The livingroom has wicker furniture and a stone fireplace. Enjoy the large wrap around deck watching the boat activity from sun up to sun down. Park of the wrap around porch is …see more

from $314 / night

$2200 / week

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Responds fast!
avg. 3 hours 18 minutes

from $314 / night

28

Cottage rental in Gloucester

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

27

Gloucester Vacation home accommodation

Cape Ann / Gloucester

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
Location, location, location! Waterviews & a short walk to Good Harbor Beach. This four bedroom/2.5 bath vacation home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach. The location offers the best of all worlds as it is so cl …see more

from $629 / night

$4400 - $4973 / week

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from $629 / night

17

Vacation home in Gloucester

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 17 minutes

from $429 / night

20

Gloucester Vacation home rental

Cape Ann / Gloucester

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
New in 2017! A riverfront property on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets you will experience from the deck or the delightful gazebo. This home has …see more

from $520 / night

$2600 - $3425 / week

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from $520 / night

37

Vacation home in Gloucester

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

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 - $3723 / week

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from $583 / night

34

Gloucester Vacation home rental

Cape Ann / Gloucester

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Rosemarc House has stairs that take you directly onto the private portion of Good Harbor Beach. This immaculate 3 bedroom, 3.5 bath luxury vacation rental home is the ultimate beach getaway. Incredible 180 degree views of the whole length of the beach, Salt Island and …see more

from $929 / night

$6500 - $10128 / week

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from $929 / night

29

Vacation cottage in Gloucester

Cape Ann / Gloucester

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • 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

21

Vacation home in Gloucester

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 - $3561 / week

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from $520 / night

23

Vacation home in Gloucester

Cape Ann / Gloucester

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 0.2 mi
  • Child friendly
  • Air conditioning
4 Bedrooms, 3 Baths (Sleeps 8) beautiful views, steps to private coffins beach Beautiful single family beach cottage, nestled among the pine trees, located on the private side of Wingaersheek Beach, which is well known as one of the most beautiful beaches on the North …see more

from $550 / night

$3850 / week

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from $550 / night

40

Vacation home in Gloucester

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 - $3052 / week

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from $470 / 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

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 - $4678 / week

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from $700 / night

34

Gloucester Vacation home rental

Cape Ann / Gloucester

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
Your family will love this extraordinary waterfront vacation rental home with spectacular views. Set on a bluff over picturesque Strawberry Cove and the open Atlantic, views abound from almost every light-filled room. The house offers three levels of sophisticated, yet …see more

from $750 / night

$3750 - $6204 / week

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from $750 / night

(2) Excellent 

7

Home rental in Gloucester with golf nearby

Cape Ann / Gloucester

5 11 1 night min

  • 5 bedrooms
  • Sleeps 11
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Turn of the century home located two blocks from Atlantic shoreline and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat. Large modern fully equipped kitchen with double oven, 6 burner stove, dishwasher, washer, …see more

from $500 / night

$3500 / week

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Responds fast!
avg. 3 hours 21 minutes

from $500 / night

19

Cottage rental in Gloucester

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

33

Vacation home in Gloucester

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 - $3111 / week

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from $450 / night

5

Vacation home in Gloucester

Cape Ann / Gloucester

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
  • Pet friendly
  • Private garden
located in quiet, wooded neighborhood. Older summer cottage close to the beach. Very comfortable for families. Good size living room for visiting. Separate dining room. Deck with small BBQ. Warm outside shower for after the beach or anytime. Close to Gloucester …see more

from $170 / night

$1190 / week

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from $170 / night

21

Vacation home rental

Cape Ann / Gloucester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Pet friendly
Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic "Gloucester Fisherman at the Wheel" sculpture -- a symbol of the fishing port's rich history as a working waterfront and …see more

from $270 / night

$1250 - $1690 / week

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from $270 / night

24

Vacation studio rental

Cape Ann / Gloucester

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Ask about children
Captain John Stephens House is a stylish and sparkling, newly remodeled studio condominium unit located in the heart of Gloucester. There are 4 units in this building and Unit 3 is on the ground floor. This bright and modern studio makes a perfect summer vacation home f …see more

from $86 / night

$600 - $950 / week

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from $86 / night

12

Gloucester Vacation home rental

Cape Ann / Gloucester

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Pet friendly
Imagine yourself walking across the lawn to the ocean, sweetly lapping the rocks. You take off your sandals and put your feet into the cool water. Second thought, jump right in! Great space for activities; near beaches, restaurants, galleries. The Space this cottage h …see more

from $350 / night

$2450 / week

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from $350 / night

(4) Very Good 

32

Home rental in Gloucester

Cape Ann / Gloucester

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Ask about children
LAST MINUTE CANCELLATION allows summer RATE DISCOUNT on authentic English Manor Home reminiscent of the Cotswolds. "Misselthwaite Manor" is a a quiet respite in a busy world, yet close to everything Historic Gloucester has to offer. Located in the heart of the pri …see more

from $379 / night

$2650 / week

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from $379 / 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

(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

11

Gloucester 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

17

Vacation home rental

Cape Ann / Gloucester

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Sun when you want it. Shade when you need it. Cool Cove is a beach house vacation rental that has it all! Sitting above Wingaersheek Beach, you will feel like you can see forever, enjoying views of Annisquam Lighthouse, Ipswich Bay, azure waters, pleasure boats, and sa …see more

from $1275 / night

$5850 - $8200 / week

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from $1275 / night

19

Gloucester Vacation home rental

Cape Ann / Gloucester

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about children
New in 2017! Enjoy views of the sun setting over the Annisquam River from this newly renovated home. It offers that "get away from it all" feeling from a combination of quiet lane, large verdant lawn with lovely plantings, and breathtaking views of the majestic A. Piatt …see more

from $350 / night

$1750 - $2200 / week

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from $350 / night

23

Gloucester Vacation home rental

Cape Ann / Gloucester

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
New in 2016! Enjoy views of Gloucester's outer harbor, and the private sandy beach, across the quiet private road from almost every room in this fantastic vacation rental home. There are two glorious slate patios that flank the front door from which you may also enjoy t …see more

from $840 / night

$4125 - $5900 / week

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from $840 / night