Location

Dates

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Vacation rentals in Marblehead, Massachusetts, United States

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

2 bedrooms·1 bath

Boston • Massachusetts

$1,507.19 USD total for 3 nights

Oct 30 – Nov 2, 2026

Bar table and Stool

Luxurious House-Harvard/PorterT 5BR/4Bath, Parking

5 bedrooms·4 baths

Somerville • Massachusetts

4.9(301 reviews)

$4,338.75 USD $3,919.88 USD total for 5 nights

Nov 13 – 18, 2026

Bedroom #1: Oversized room with king sized bed, plenty of reading material, and a white noise machine for a comfortable night’s rest.

Bedroom #1 has a book nook with plenty of reading material for all ages!

Bedroom #2: Another spacious king-sized bed with desk in oversized room.

Fully stocked kitchen with coffee maker, kettle, washer / dryer.

We hope you have sunny weather - but we have umbrellas and a coat tree for wet / snowy days.

Superhost: King Beds! * Kid Friendly. You're Home.

2 bedrooms·1 bath

Boston • Massachusetts

5(216 reviews)

$1,181.55 USD total for 3 nights

Nov 1 – 4, 2026

Bedroom – King Bed & Fantastic City View Seating

Cozy King Bedroom with TV

Cozy King Bedroom with TV

Classy Queen Bedroom

Open Living Area

Modern Luxury 2BR | King + Queen | Suite 8

2 bedrooms·1 bath

Boston • Massachusetts

$1,160.04 USD total for 3 nights

Nov 9 – 12, 2026

Bedroom – King Bed & Fantastic City View Seating

Cozy King Bedroom with TV

Cozy King Bedroom with TV

Classy Bedroom Queen Bedroom

Open Living Area

Family Cove: Quiet & Modern 2 bed | Suite 10

2 bedrooms·1 bath

Boston • Massachusetts

$1,596.25 USD total for 3 nights

Oct 30 – Nov 2, 2026

Bedroom – King Bed & Fantastic City View Seating

Cozy King Bedroom with TV

Bedroom 1 – King Bed & TV

Classy Bedroom Queen Bed

Sleek Modern 2 Bed: King + Queen | Suite 6

2 bedrooms·1 bath

Boston • Massachusetts

$1,943.58 USD total for 3 nights

Nov 18 – 21, 2026

Cozy King Bedroom

Cozy King Bedroom

Enjoy the view from the large bay windows in the sitting area

Relaxing Den Area with Pull Out Seating

Relaxing Den Area – TV & Pull Out Seating

Elegant 1BR Plus: Cityscape Views + King and pull out Queen| Suite 5

2 bedrooms·1 bath

Boston • Massachusetts

$1,314.56 USD total for 3 nights

Oct 30 – Nov 2, 2026

Cozy King Bedroom

Amazing city views from the large bay windows in the sitting area

Cozy King Bedroom with City View

Modern Comfort Living Area – Pull Out Seating

Modern Comfort Living Area – TV & Pull Out Seating

Elegant 1BR Plus: Sky-High City Views + King | Suite 9

2 bedrooms·1 bath

Boston • Massachusetts

$1,685.13 USD total for 3 nights

Nov 2 – 5, 2026

City View Bedroom – King Bed

Fantastic City View Seating

Bedroom – King Bed

Living Area – TV & Seating

Open Living Area

Front Row City Views: 1BR Suite with King Bed | Suite 3

1 bedroom·1 bath

Boston • Massachusetts

$1,285.84 USD total for 3 nights

Nov 7 – 10, 2026

King size master bed with privacy curtains

King size bed with all comforts

Lofty open space

Open space layout keeps everyone together weather in the kitchen or livingroom

Livingroom featuring a large TV

The Urban Hideout Loft: Sleeps 4 | Private Entrance

0 bedrooms·1 bath

Boston • Massachusetts

$1,295.42 USD total for 3 nights

Nov 1 – 4, 2026

Cozy King Bedroom

Fantastic City View Seating from the large bay windows

Cozy King Bedroom with City View

Relaxing Den Area with Pull Out Seating

Relaxing Den Area – TV & Pull Out Seating

Cityscape 1BR Plus: King + Queen Pull-out | Suite 7

2 bedrooms·1 bath

Boston • Massachusetts

$1,352.85 USD total for 3 nights

Nov 1 – 4, 2026

Bedroom 1 – King Bed

Bedroom – King Bed & TV

Bedroom – King Bed

Bedroom 2 – Queen Bed

Bedroom – Queen Bed

Trendy 2BR Plus Family Getaway | Suite 4

2 bedrooms·1 bath

Boston • Massachusetts

$2,282.69 USD total for 3 nights

Nov 3 – 6, 2026

Bedroom – King Bed

Bedroom – King Bed

Open Living Area

Open Living & Kitchen Area

Living Room – Sofa Bed

Luxury 1BR: Sleek Kitchen + City Charm | Suite 2

1 bedroom·1 bath

Boston • Massachusetts

$1,314.56 USD total for 3 nights

Nov 1 – 4, 2026

Anchor's Away @ The Sail Loft!

Living room with dining table

Comfortable chair

View out windows to White Wharf

"Rockport Sail Loft: 2 Bed/1 Bath Oceanfront Haven

2 bedrooms·1 bath

Rockport • Massachusetts

4.87(143 reviews)

$1,160.10 USD total for 3 nights

Oct 31 – Nov 3, 2026

Living Room: Bright space with nautical charm, leather couch, and dining for four! Perfect for relaxing!

Living Room: Relax in style with plush seating, vintage decor, and warm natural light!

Views of Bearskin neck and peeks of the Harbor from windows

Living Room: Sunlight dances through windows, inviting relaxation in stylish comfort and charm!

Bedroom 1 -Queen Bed

The Waterline

2 bedrooms·1 bath

Rockport • Massachusetts

5(17 reviews)

$867.85 USD total for 3 nights

Oct 31 – Nov 3, 2026

Sunny 1st floor unit with views

Smart TV in living room for streaming

Leather arm chairs

The Orca

2 bedrooms·1 bath

Rockport • Massachusetts

5(11 reviews)

$723.01 USD total for 3 nights

Nov 3 – 6, 2026

Living Room: Timber beams and natural light create a vibrant space for relaxation and fun!

Living Room: Bright and airy space with unique decor, perfect for relaxation and coastal views!

Living Room: Timber beams and a blend of vintage charm invite relaxation and great conversations!

Bedroom: Charming retreat illuminated by natural light with rustic beams and delightful decor!

Bar style eating counter overlooking Bearskin beck

The Captain's Quarters

2 bedrooms·1 bath

Rockport • Massachusetts

4.83(160 reviews)

$769.69 USD total for 3 nights

Nov 1 – 4, 2026

Charming Loft Kitchen: Enjoy culinary adventures in a sunlit space with rustic beams and modern flair!

The Crow's Nest

The Crow's Nest

The Crow's Nest

The Crow's Nest

The Crow's Nest

1 bedroom·1 bath

Rockport • Massachusetts

5(5 reviews)

$702.64 USD total for 3 nights

Nov 1 – 4, 2026

living and dining area

First floor full bathroom

Boston Historical Urban Oasis

7 bedrooms·3 baths

Boston • Massachusetts

$2,394.94 USD total for 3 nights

Nov 3 – 6, 2026

Eating area and sleeping area

Kitchen After 2025 Renovation showing clothes washer-dryer

Back yard from back deck

House From Street

Cambridge Studio Apartment

1 bedroom·1 bath

Cambridge • Massachusetts

4.67(400 reviews)

$150/ night(excl. fees & taxes)

3BR Retreat · Sleeps 8 · Coolidge Corner T image 1

3BR Retreat · Sleeps 8 · Coolidge Corner T image 2

3BR Retreat · Sleeps 8 · Coolidge Corner T image 3

3BR Retreat · Sleeps 8 · Coolidge Corner T image 4

3BR Retreat · Sleeps 8 · Coolidge Corner T image 5

3BR Retreat · Sleeps 8 · Coolidge Corner T

3 bedrooms·1 bath

Brookline • Massachusetts

4.5(2 reviews)

$1,347.00 USD total for 3 nights

Nov 2 – 5, 2026

Bedroom #1 Queen bed

Bedroom #2 with queen bed and crib

Boston's Jamaica Plain w/ parking, A/C, laundry

2 bedrooms·1 bath

Boston • Massachusetts

4.81(120 reviews)

$876.75 USD total for 3 nights

Nov 9 – 12, 2026

Oceanside | Family Friendly Oceanfront Home

Oceanside | Family Friendly Oceanfront Home

Oceanside | Family Friendly Oceanfront Home

Oceanside | Family Friendly Oceanfront Home

Oceanside | Family Friendly Oceanfront Home

Oceanside | Family Friendly Oceanfront Home

4 bedrooms·2 baths

Scituate • Massachusetts

5(104 reviews)

$1,533.00 USD total for 4 nights

Oct 30 – Nov 3, 2026

Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

3 bedrooms·2 baths

Billerica • Massachusetts

$1,598.72 USD total for 3 nights

Oct 30 – Nov 2, 2026