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Gloucester Rentals

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Results: 232 Rentals

  • Airstream & Ocean View: Unique Gloucester Getaway
    From $269 per night (USD)

    VRBO

    Airstream & Ocean View: Unique Gloucester Getaway

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    5 Acres | Close to Beaches & Trails | Pet Friendly (w/ Fee) | Apartment + Airstream 'Glamping' with a modern twist, thi ...

    From $269 per night (USD)

    VRBO

    Details
  • The Gallery: Rocky Neck Waterfront
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    Expedia

    The Gallery: Rocky Neck Waterfront

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Please note that The Gallery has a one month (31 night) minimum rental period. Welcome to The Gallery, a stunning water ...

    Click For Pricing

    Expedia

    Details
  • Portside Glimpse: Peekaboo Views of Front Beach
    From $353 per night (USD)

    VRBO

    Portside Glimpse: Peekaboo Views of Front Beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Get away to this modern one-bedroom apartment located in the heart of downtown Rockport. Portside Glimpse is a bright an ...

    From $353 per night (USD)

    VRBO

    Details
  • Oceanfront Dock Escape ~ Kayaks & Paddleboards
    From $591 per night (USD)

    Expedia

    Oceanfront Dock Escape ~ Kayaks & Paddleboards

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Summary: This 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, M ...

    From $591 per night (USD)

    Expedia

    Details
  • Beautifully renovated home walk to boulevard, town & train
    From $357 per night (USD)

    VRBO

    Beautifully renovated home walk to boulevard, town & train

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Longview House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...

    From $357 per night (USD)

    VRBO

    Details
  • Portside Overlook: Village and Beach Views!
    From $587 per night (USD)

    Expedia

    Portside Overlook: Village and Beach Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Get away to this modern two-bedroom apartment located in the heart of downtown Rockport. With ocean views and decks on t ...

    From $587 per night (USD)

    Expedia

    Details
  • Painter's Perch: Rocky Neck
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    VRBO

    Painter's Perch: Rocky Neck

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Sitting high above Rocky Neck, Painter’s Perch offers stunning views of the Neck and picturesque Smith Cove. This charmi ...

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    VRBO

    Details
  • Stay at Little River
    From $369 per night (USD)

    Expedia

    Stay at Little River

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    7

    Summary: ✔ Waterfront Location – Nestled on picturesque Little River with peaceful views ✔ Sleeps 7 – 1 King • 1 Queen • ...

    From $369 per night (USD)

    Expedia

    Details
  • Rocky Neck waterfront 2 bed 2 bath apt walk to the beach, restaurants, galleries
    From $391 per night (USD)

    VRBO

    Rocky Neck waterfront 2 bed 2 bath apt walk to the beach, restaurants, galleries

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Nestled in the Rocky Neck waterfront, this updated apartment boasts 2 bedrooms - one with a queen bed and the other day ...

    From $391 per night (USD)

    VRBO

    Details
  • Stay at Rocky Neck Su
    From $474 per night (USD)

    Expedia

    Stay at Rocky Neck Su

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Summary: Rare Gloucester Waterfront Retreat! ✓ Perched directly on the water with breathtaking ocean views ✓ Expansive ...

    From $474 per night (USD)

    Expedia

    Details
  • 4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included
    From $421 per night (USD)

    VRBO

    4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    KEY FEATURES: ☆Entire 2 story fully renovated home that sleeps 8 adults comfortably ☆Private backyard with a gas grill a ...

    From $421 per night (USD)

    VRBO

    Details
  • Mill Brook House: A Colonial Original
    From $581 per night (USD)

    Expedia

    Mill Brook House: A Colonial Original

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Nestled in the heart of historic Rockport, Mill Brook House beautifully blends timeless charm with modern conveniences. ...

    From $581 per night (USD)

    Expedia

    Details
  • Life of Reilly - Private & Serene Rockport Escape
    From $436 per night (USD)

    VRBO

    Life of Reilly - Private & Serene Rockport Escape

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    New for Summer 2025! Life of Reilly is a stylish 2-bedroom, 1.5-bathroom vacation home tucked away on a serene 4.5-acre ...

    From $436 per night (USD)

    VRBO

    Details
  • Charming Waterfront 1 bedroom apartment in wonderful E. Gloucester with WiFi, AC
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    Expedia

    Charming Waterfront 1 bedroom apartment in wonderful E. Gloucester with WiFi, AC

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy a peaceful stay at this delightful 1-bedroom apartment in RockyNeck, Gloucester. The cozy bedroom features 1 full ...

    Click For Pricing

    Expedia

    Details
  • 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
    From $390 per night (USD)

    VRBO

    3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    KEY FEATURES: * 2 story townhouse that sleeps 8 comfortably * Walking distance to beaches and Downtown Gloucester *Fully ...

    From $390 per night (USD)

    VRBO

    Details
  • Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24
    From $1814 per night (USD)

    Expedia

    Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

    Bedrooms:
    7
    Bathrooms:
    9
    Sleeps:
    24

    *MORE PHOTOS COMING SOON ☀ Sleeps 24 guests across 9 bedrooms ☀ Perched on the Back Shore ~ 1 mile or 5min drive to Good ...

    From $1814 per night (USD)

    Expedia

    Details
  • Tidebend: River views and gracious comfort
    From $738 per night (USD)

    VRBO

    Tidebend: River views and gracious comfort

    Bedrooms:
    2
    Bathrooms:
    6
    Sleeps:
    10

    Welcome to Tidebend, your next Gloucester escape! This stunning 6-bedroom, 2.5-bath home overlooks the picturesque Annis ...

    From $738 per night (USD)

    VRBO

    Details
  • River view home w/ deck, river access, near beaches and train
    From $499 per night (USD)

    Expedia

    River view home w/ deck, river access, near beaches and train

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Little River Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...

    From $499 per night (USD)

    Expedia

    Details
  • Stay at Smith Cove Su
    From $457 per night (USD)

    VRBO

    Stay at Smith Cove Su

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    7

    Summary: Rare Gloucester Waterfront Retreat! ✓ Rocky Neck Location – Nestled above scenic Smith Cove with breathtaking ...

    From $457 per night (USD)

    VRBO

    Details
  • \nCozy 1-bedroom apartment in charming Gloucester overlooking a small beach.
    From $376 per night (USD)

    Expedia

    \nCozy 1-bedroom apartment in charming Gloucester overlooking a small beach.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Relax in the soothing ambiance after a day of exploring some of our fine restaurants and shops among other fine attract ...

    From $376 per night (USD)

    Expedia

    Details
  • Charming 2nd floor apartment on Lane's Cove
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    VRBO

    Charming 2nd floor apartment on Lane's Cove

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Our charming oceanside apartment in the picturesque village of Lanesville is perfectly situated on the edge of Lanes Cov ...

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    VRBO

    Details
  • Charming bungalow with pool! Walk to Front Beach and shops! Sep-Oct Availability
    From $449 per night (USD)

    Expedia

    Charming bungalow with pool! Walk to Front Beach and shops! Sep-Oct Availability

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    We are the delighted new owners of this well established & well loved short term rental! This Rockport bungalow sits on ...

    From $449 per night (USD)

    Expedia

    Details
  • Close to Good Harbor Beach, 3 bedroom apartment
    From $358 per night (USD)

    VRBO

    Close to Good Harbor Beach, 3 bedroom apartment

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Located in a quiet neighborhood within a half mile of Good Harbor Beach, relax and enjoy the beauty of Gloucester. The ...

    From $358 per night (USD)

    VRBO

    Details
  • Stay at The Neck Summ
    From $439 per night (USD)

    Expedia

    Stay at The Neck Summ

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Summary: ✓ Smith Cove Views – Perched above the harbor with sweeping water & neighborhood scenery ✓ Two Spacious Decks – ...

    From $439 per night (USD)

    Expedia

    Details
  • cottage close to long beach and good harbor
    From $454 per night (USD)

    VRBO

    cottage close to long beach and good harbor

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Summer at its best! A delightful spot near the beach with nice private backyard, walkable to Long Beach and Good Harbor ...

    From $454 per night (USD)

    VRBO

    Details
  • Spacious Retreat Near Good Harbor Beach
    From $500 per night (USD)

    VRBO

    Spacious Retreat Near Good Harbor Beach

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Summary: Just a quick 15-minute walk to the Little Good Harbor footbridge, this spacious 4-bedroom home sleeps 10 and fe ...

    From $500 per night (USD)

    VRBO

    Details
  • Spy Glass - Views of Ipswich Bay
    From $310 per night (USD)

    VRBO

    Spy Glass - Views of Ipswich Bay

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    New for 2025! Perched on the third floor of a well-maintained building, this modern two-bedroom apartment offers comfort ...

    From $310 per night (USD)

    VRBO

    Details
  • Stay at East Gloucester
    From $312 per night (USD)

    Expedia

    Stay at East Gloucester

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    7

    Summary: Charming East Gloucester Home ✓ Prime Location – Walk to beaches, parks & local attractions ✓ Outdoor Retreat ...

    From $312 per night (USD)

    Expedia

    Details
  • Bell View: Private tennis court and an in-law
    From $1253 per night (USD)

    VRBO

    Bell View: Private tennis court and an in-law

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    17

    Your Gloucester vacation experience awaits you in this spacious and versatile vacation home. Bell View can accommodate u ...

    From $1253 per night (USD)

    VRBO

    Details
  • Tranquil 7-bedroom house with Ocean views in Gloucester's charming Rocky Neck
    From $1424 per night (USD)

    VRBO

    Tranquil 7-bedroom house with Ocean views in Gloucester's charming Rocky Neck

    Bedrooms:
    3
    Bathrooms:
    7
    Sleeps:
    18

    Escape to this beautiful Home nestled in the heart of Rocky Neck. This home boasts newly renovated interiors adorned wit ...

    From $1424 per night (USD)

    VRBO

    Details
  • Canal Water View; Steps to Ocean, Boulevard, Park
    From $340 per night (USD)

    VRBO

    Canal Water View; Steps to Ocean, Boulevard, Park

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your charming waterfront retreat in central downtown Gloucester! This delightful 2-bedroom, 1-bathroom apartm ...

    From $340 per night (USD)

    VRBO

    Details
  • Guest House on Private Estate with Beach
    From $383 per night (USD)

    Expedia

    Guest House on Private Estate with Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to this charming Gloucester home! This delightful 2-bedroom, 1-bath guest home is perfect for families. Enjoy a ...

    From $383 per night (USD)

    Expedia

    Details