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Manchester-by-the-Sea Vacation Rentals

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49 rentals in Manchester-by-the-Sea.
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Booth Cottage: Walk down a private path to fabled Singing Beach., vacation rental in Manchester-by-the-Sea

Booth Cottage: Walk down a private path to fabled Singing Beach.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The Cottage, vacation rental in Manchester-by-the-Sea

The Cottage

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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4 Bedroom LUX House/with Pool Next Door, vacation rental in Manchester-by-the-Sea

4 Bedroom LUX House/with Pool Next Door

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sweeping Harbor Views, Private Deck, Historic District, Walk To Everything!, vacation rental in Manchester-by-the-Sea

Sweeping Harbor Views, Private Deck, Historic District, Walk To Everything!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Marblehead Townhouse - Roof Deck with Panoramic Views, vacation rental in Manchester-by-the-Sea

Spacious Marblehead Townhouse - Roof Deck with Panoramic Views

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Downtown apartment in historic Marblehead, only a short walk to harbor, vacation rental in Manchester-by-the-Sea

Downtown apartment in historic Marblehead, only a short walk to harbor

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Walkable to Everything that is Great about Marblehead!  Beaches & Pond nearby, vacation rental in Manchester-by-the-Sea

Walkable to Everything that is Great about Marblehead! Beaches & Pond nearby

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach, vacation rental in Manchester-by-the-Sea

Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Walk to downtown Gloucester & Pavilion Beach!, vacation rental in Manchester-by-the-Sea

Walk to downtown Gloucester & Pavilion Beach!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Romantic SUMMERWIND COTTAGE- Scenic Harbor View, vacation rental in Manchester-by-the-Sea

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Welcoming Getway Oasis, vacation rental in Manchester-by-the-Sea

Welcoming Getway Oasis

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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In the Heart of the Historic District, vacation rental in Manchester-by-the-Sea

In the Heart of the Historic District

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA, vacation rental in Manchester-by-the-Sea

Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning SUNSET STUDIO w/Scenic Harbor View, vacation rental in Manchester-by-the-Sea

Stunning SUNSET STUDIO w/Scenic Harbor View

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Harborfront, Beverly/Salem, Boston North Shore, vacation rental in Manchester-by-the-Sea

The Harborfront, Beverly/Salem, Boston North Shore

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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La Bohème RETREAT Studio, vacation rental in Manchester-by-the-Sea

La Bohème RETREAT Studio

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Lovely 'Blue Heron Cottage' on Annisquam River!, vacation rental in Manchester-by-the-Sea

Lovely 'Blue Heron Cottage' on Annisquam River!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Coastal, Cute & Cozy|Close to Everything, vacation rental in Manchester-by-the-Sea

Coastal, Cute & Cozy|Close to Everything

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Savor Spring: private garden! Brackett Cottage: Fast WiFi, charming walk to shop, vacation rental in Manchester-by-the-Sea

Savor Spring: private garden! Brackett Cottage: Fast WiFi, charming walk to shop

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches, vacation rental in Manchester-by-the-Sea

Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Ipswich Cottage w/Beautiful Views, 5 Mins to Beach, vacation rental in Manchester-by-the-Sea

Ipswich Cottage w/Beautiful Views, 5 Mins to Beach

4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Annisquam Singing Pines: Private riverfront setting & tidal dock., vacation rental in Manchester-by-the-Sea

Annisquam Singing Pines: Private riverfront setting & tidal dock.

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Sea Fox: Custom-designed home with rights to private Coffins Beach, vacation rental in Manchester-by-the-Sea

Sea Fox: Custom-designed home with rights to private Coffins Beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Clamshell Landing: Bring your game to its squash & tennis courts!, vacation rental in Manchester-by-the-Sea

Clamshell Landing: Bring your game to its squash & tennis courts!

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Bell View: Private tennis court and an in-law suite., vacation rental in Manchester-by-the-Sea

Bell View: Private tennis court and an in-law suite.

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Magnolia Tides: Multi-level waterfront home, vacation rental in Manchester-by-the-Sea

Magnolia Tides: Multi-level waterfront home

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Thurston Point: Waterfront rental with deepwater dock on Annisquam River!, vacation rental in Manchester-by-the-Sea

Thurston Point: Waterfront rental with deepwater dock on Annisquam River!

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom), vacation rental in Manchester-by-the-Sea

Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom)

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perrywinkle: Waterfront on Gloucester’s Rocky Neck., vacation rental in Manchester-by-the-Sea

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Exclusive Lifestyle near the Ocean, vacation rental in Manchester-by-the-Sea

Exclusive Lifestyle near the Ocean

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Family Tides: Only a half-mile from Good Harbor Beach., vacation rental in Manchester-by-the-Sea

Family Tides: Only a half-mile from Good Harbor Beach.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautifully Appointed Home in Old Town, vacation rental in Manchester-by-the-Sea

Beautifully Appointed Home in Old Town

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Wonder, vacation rental in Manchester-by-the-Sea

Waterfront Wonder

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf, vacation rental in Manchester-by-the-Sea

Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Downtown Beverly Cozy 2bedroom, vacation rental in Manchester-by-the-Sea

Downtown Beverly Cozy 2bedroom

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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RiverView: Family Fun! Waterfront Neighborhood Park, Boston Train, Pubs & Shops,, vacation rental in Manchester-by-the-Sea

RiverView: Family Fun! Waterfront Neighborhood Park, Boston Train, Pubs & Shops,

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Special Rate: Rockmere Inn: 3 King Suites, Fast WiFi, Private Garden, Walk to wa, vacation rental in Manchester-by-the-Sea

Special Rate: Rockmere Inn: 3 King Suites, Fast WiFi, Private Garden, Walk to wa

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Marblehead Neck Ocean View Cottage, vacation rental in Manchester-by-the-Sea

Marblehead Neck Ocean View Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe., vacation rental in Manchester-by-the-Sea

Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Quaint Beverly Townhome: Walk to Beach & Downtown!, vacation rental in Manchester-by-the-Sea

Quaint Beverly Townhome: Walk to Beach & Downtown!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Plaisance - Enjoy the best of Gloucester living., vacation rental in Manchester-by-the-Sea

Plaisance - Enjoy the best of Gloucester living.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Terra Nova Cottage, vacation rental in Manchester-by-the-Sea

Terra Nova Cottage

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck., vacation rental in Manchester-by-the-Sea

Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Mount: Walk to Niles Beach & Rocky Neck from this elegant home., vacation rental in Manchester-by-the-Sea

The Mount: Walk to Niles Beach & Rocky Neck from this elegant home.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Inviting Apartment Near Waterfront & Museums!, vacation rental in Manchester-by-the-Sea

NEW! Inviting Apartment Near Waterfront & Museums!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sweet Retreat: Walk to Waterfront, Shops, & Eateries - Off Street Parking, Smart, vacation rental in Manchester-by-the-Sea

Sweet Retreat: Walk to Waterfront, Shops, & Eateries - Off Street Parking, Smart

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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River Watch: Waterfront rental home with views and private dock., vacation rental in Manchester-by-the-Sea

River Watch: Waterfront rental home with views and private dock.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Bray Cottage: A charming cottage close to Wingaersheek Beach., vacation rental in Manchester-by-the-Sea

Bray Cottage: A charming cottage close to Wingaersheek Beach.

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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River's Edge: A charming 2BR riverfront home in Gloucester., vacation rental in Manchester-by-the-Sea

River's Edge: A charming 2BR riverfront home in Gloucester.

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely Downtown Beverly, vacation rental in Manchester-by-the-Sea

Lovely Downtown Beverly

3 bedrooms
1 bathroom
Sleeps 1
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