50 Best Rockport Apartments on Holiday Lettings - Vacation rentals

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67 Vacation rentals

15

Vacation home in Rockport

Cape Ann / Rockport

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
New in 2017! Ideally situated just a short stroll from Old Garden Beach and the historic and quaint oceanfront village of Rockport, Beach Bound is a delightful and newly constructed 4 bedroom, 2.5 bath vacation home. Relax on the lovely back deck enjoying the home’s ser …see more

from $640 / night

$3200 - $3500 / week

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from $640 / 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 $183 / night

$1275 - $1346 / week

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Responds fast!
avg. 51 minutes

from $183 / night

29

Vacation home rental

Cape Ann / Rockport

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Boasting stunning views only imaginable from a home with direct water frontage, Spindrift, a 4+ bedroom, 2+ bath vacation rental home is located in Rockport’s lovely South End. It is the perfect location for rest and relaxation. According to the Oxford English Dictio …see more

from $750 / night

$4500 - $4578 / week

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from $750 / night

(1) Excellent 

16

Home rental in Rockport

Cape Ann / Rockport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
This delightful vacation rental cottage is located on a quiet Rockport lane less than 100 yards from the sands of Cape Hedge Beach. Just cross the lane and walk over the footbridge and you're on the beach! This cozy two bedroom beach house is pine-paneled, in the tra …see more

from $283 / night

$1375 - $1815 / week

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from $283 / night

(3) Excellent 

14

Rockport 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 49 minutes

from $135 / night

32

Vacation home in Rockport

Cape Ann / Rockport

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This waterfront historic vacation home is centrally located in the village of Rockport and was home to John Oakes in the late 18th and early 19th centuries. Completely renovated in 2015 and brought up to the highest modern standard, it retains its old world charm. It ha …see more

from $403 / night

$2815 - $3764 / week

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from $403 / night

(5) Excellent 

21

Vacation apartment in Rockport

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 

17

Vacation home in Rockport

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

$3651 / week

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from $400 / night

(1) Excellent 

28

Rockport Vacation home rental

Cape Ann / Rockport

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
Enjoy the best of all worlds in this spacious and bright vacation rental home overlooking Rockport's stunningly picturesque Flat Ledge Quarry. Not only can you walk to town or to the beach in a few minutes, but the property includes full deeded swimming rights to Little …see more

from $440 / night

$2200 - $2900 / week

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from $440 / night

11

Vacation home in Rockport

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

28

Vacation home in Rockport

Cape Ann / Rockport

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
New in 2017! Breathtakingly spectacular views from the living room and deck will keep you riveted to your lounge chair for most of your stay. The rest of the house is pretty amazing as well, with exquisite ocean views from just about every room. When you are ready to g …see more

from $1150 / night

$6501 - $7018 / week

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from $1150 / night

25

Vacation home in Rockport

Cape Ann / Rockport

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
New in 2016! Enjoy the comforts of modern day living while you step back in time in this updated colonial-era vacation rental home. From the moment you turn the brass door knob, which is original to the house, you will feel steeped in history. Filled with light from t …see more

from $300 / night

$1650 - $2300 / week

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from $300 / 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

$450 - $3500 / week

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from $567 / night

16

Cottage rental in Rockport

Cape Ann / Rockport

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Pet friendly
From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or walk down the quiet lane to Granite Pier and experience the unsurpassed views of the sun rising over the Atlantic Ocean, and of fishing boats moored nearby. The full moon over Granite Pier …see more

from $220 / night

$1100 - $1450 / week

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from $220 / night

28

Vacation cottage in Rockport

Cape Ann / Rockport

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
This sweet and comfortable vacation rental cottage is just across the street from Folly Cove, one of the most striking coves on Cape Ann. The living room has views of the water (just across the street) and off of the living room is a nice screened porch with views an …see more

from $330 / night

$1400 - $2100 / week

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from $330 / night

38

Vacation home in Rockport

Cape Ann / Rockport

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Pet friendly
This waterfront vacation rental is a wonderful inviting family vacation home with bountiful space, located in the highly desirable area of "The Avenues" at the northern end of Rockport. Boasting 5 bedrooms/3.5 baths and the ability to comfortably sleep 12 people, this i …see more

from $780 / night

$3900 - $5500 / week

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from $780 / night

23

Rockport Vacation cottage rental

Cape Ann / Rockport

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This sweet 2 bedroom vacation rental cottage is the perfect place to be this summer, as it is all about the sun, sand and surf of wonderful mile long - Long Beach, which is just about 25 yards from the cottage. The cottage is all on one level, with a wonderful sun po …see more

from $186 / night

$1300 - $1750 / week

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from $186 / night

33

Vacation home in Rockport

Cape Ann / Rockport

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
Rockport oceanfront! This sunny and immaculate vacation rental home couldn’t be closer to the water, situated on a bluff overlooking Sandy Bay and Pigeon Cove Harbor. Popples Cove House offers everything you could hope for in a vacation getaway – scenic views, location, …see more

from $667 / night

$3200 - $4400 / week

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from $667 / night

(27) Excellent 

23

Vacation cottage with golf nearby in Rockport

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 - $1050 / week

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from $125 / night

31

Vacation home in Rockport

Cape Ann / Rockport

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Pet friendly
This inviting family vacation home has bountiful space and is located in the highly desirable area of "The Avenues" at the northern end of Rockport. Boasting 6 bedrooms, 3.5 baths and the ability to comfortably sleep 10 people, this is a house for the extended family to …see more

from $546 / night

$2400 - $3400 / week

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from $546 / night

35

Home rental in Rockport

Cape Ann / Rockport

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
This immaculate beachfront vacation home has been completely remodeled but retains hints of its historical importance; it was the original U.S. base for the first Trans-Atlantic Cable in 1884. Originating in Ireland, the cable went from Nova Scotia to Cape Ann and back …see more

from $850 / night

$3750 - $5188 / week

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from $850 / night

24

Vacation home rental

Cape Ann / Rockport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
This spacious 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 elec …see more

from $608 / night

$2725 - $3713 / week

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from $608 / night

29

Vacation cottage in Rockport

Cape Ann / Rockport

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children
  • Pet friendly
This utterly sweet vacation rental cottage overlooking Rockport's beautiful Folly Cove has all modern amenities but maintains the ambiance of the year 1805, when it was built. A thoughtful eye has preserved the property's historical integrity while adding modern comfort …see more

from $270 / night

$1175 - $1626 / week

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from $270 / night

(6) Excellent 

24

Rockport Vacation apartment rental

Cape Ann / Rockport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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

$995 - $2443 / week

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from $199 / night

36

Rockport Vacation home rental

Cape Ann / Rockport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
This waterfront vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor with unobstructed 180 degree views of the Atlantic, Sandy Bay, and the twinkling lights of the village of Rockport. The location of the home is ideal, away from all the hustle of to …see more

from $730 / night

$3651 - $5225 / week

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from $730 / night

22

Vacation home rental

Cape Ann / Rockport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
Midway between two picturesque places, the seaside village of Rockport and the historic fishing port of Gloucester, Sage Hill is the perfect vacation destination. Walk to Long Beach (it’s about a 5 minute walk), or take a short drive to Good Harbor Beach. Sage Hill …see more

from $438 / night

$2000 - $2750 / week

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from $438 / night

(2) Very Good 

12

Vacation home in Rockport

Cape Ann / Rockport

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Car not necessary
  • Air conditioning
  • Private garden
Beachcomber Room, at Changing Tides Bed and Breakfast, features a comfortable king sized bed or 2 twin beds, and an ensuite bathroom. This sunny room has 2 sky lights, a ceiling fan, AC, a sitting room with a small refrigerator, and a shared bathroom. Stay includes da …see more

from $140 / night

$892 / week

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Responds fast!
avg. 2 hours 49 minutes

from $140 / night

22

Vacation home in Rockport

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

(2) Excellent 

15

Vacation b&b in Rockport

Cape Ann / Rockport

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
  • Private garden
Are you looking for an affordable place to stay while you enjoy all that Rockport has to offer? Are you traveling with family or friends and would like the privacy of separate rooms? Our top floor guest rooms (2 available) are perfect for travelers on a budget. Clean …see more

from $95 / night

$665 / week

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Responds fast!
avg. 2 hours 24 minutes

from $95 / night

28

Vacation home in Rockport

Cape Ann / Rockport

3 12 Min stay varies

  • 3 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning
Enjoy the amazing views of the ever changing Atlantic Ocean and Rockport's Thatcher Island with its twinkling twin lighthouses from this multi-level year round Rockport home . Vacation here in all the seasons by the weekend, week or month. Views abound from the living …see more

from $640 / night

$3200 - $4400 / week

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from $640 / night

(5) Excellent 

15

Vacation b&b in Rockport

Cape Ann / Rockport

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 24 minutes

from $125 / night

28

Vacation home in Rockport

Cape Ann / Rockport

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
This gorgeous in-town Victorian vacation rental home offers the best of all worlds; it has been beautifully renovated, but it retains the old-world charm of 14 foot ceilings, huge windows and large rooms. Modern updates include all new baths, windows, refinished hardwoo …see more

from $689 / night

$2900 - $4125 / week

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from $689 / night

15

Rockport Vacation apartment rental

Cape Ann / Rockport

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
The Building was once the historic Sail loft- oozing with character and charm. Inside is a 2 Bedroom, 1 Bath apartment unit. A good sized living area with a leather couch, TV & dining table that can fit up to 6. There is a small patio in front with a table, bench and 2 …see more

from $145 / night

$850 / week

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from $145 / night

31

Home accommodation in Rockport

Cape Ann / Rockport

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
This charming vacation rental home is ideally situated just 300 yards from the waterfront, as well as a short walk (1 mile) to a sandy beach, and the picturesque village of Rockport with its shops, restaurants, galleries and the world class Shalin Liu Performance Cente …see more

from $396 / night

$1650 - $2400 / week

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from $396 / night

19

Vacation apartment in Rockport

Cape Ann / Rockport

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children
  • Pet friendly
New in 2017! Views. All that Rockport has to offer is within a short walk from this completely remodeled property located in the picturesque Historic District. This vacation rental home gleams with modern amenities yet retains the charm of the original house, which date …see more

from $267 / night

$1600 - $1692 / week

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from $267 / night

(3) Excellent 

18

Vacation home in Rockport

Cape Ann / Rockport

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Located across from Rockport's Front Beach, Beach & King Beach House is an intimate Cape Ann home located on the North Shore in Massachusetts. Accommodations at our Rockport home offer a picturesque setting with stunning ocean views and a 5-minute stroll to historic Bea …see more

from $615 / night

$4300 - $7800 / week

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from $615 / night

(1)  

41

Vacation home in Rockport

Cape Ann / Rockport

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
From its waterfront perch, this 4BR vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor and has spectacular, unobstructed views of Sandy Bay. The location of the home is ideal, away from all the hustle of town, but within a 10-15 minute walk to ever …see more

from $650 / night

$3150 - $4675 / week

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from $650 / night

21

Vacation home in Rockport

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

(1) Excellent 

14

Vacation cottage accommodation

Cape Ann / Rockport

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Walk to the water from this cozy peaceful cottage with ocean views. This bright and cheerful recently updated vintage cottage is just minutes from nearby beaches. Enjoy beautiful sunrises, birds chirping, and leisurely strolls along the rugged coast. Stunning views of t …see more

from $180 / night

$1280 - $1400 / week

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from $180 / night

15

Vacation home rental

Cape Ann / Rockport

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Private garden
$1,600 (off season) - $2,100 (peak season) per week .... Fresh sea breezes keep the inside cool during the summer and a large fireplace in the living room makes this a cozy winter getaway. The home comfortably sleeps five, has a completely furnished kitchen, a dining ro …see more

from $229 / night

$1600 / week

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from $229 / night