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Vacation rentals in Massachusetts

New mid century modern style furniture with oceanfront views from the living room

Oceanfront cottage on a private beach

Your own private path to the beach

You can't get any closer to the your own private beach!

Beach chairs are provided! Ready for you to step out of your car and right onto the beach! No parking worries, always cold beverages and quick access to your own bathroom. A++ Beach towels are not provided.

Sand Castle Drive ~ Oceanfront with Private Beach

2 bedrooms·1 bath

Sandwich • Massachusetts

4.93(28 reviews)

$406/ night(excl. fees & taxes)

New flooring (2022)

Vaulted Ceiling

Oceanfront Penthouse Salisbury

5 bedrooms·2 baths

Salisbury • Massachusetts

5(182 reviews)

$1,503.00 USD total for 3 nights

Oct 20 – 23, 2026

Maushop Village Cottage

Maushop Village Cottage

Maushop Village Cottage

Maushop Village Cottage

Maushop Village Cottage

Maushop Village Cottage

2 bedrooms·1½ baths

Mashpee • Massachusetts

$4,800.00 USD total for 7 nights

Oct 19 – 26, 2026

Game room with shuffle board, ski ball, air hockey and ping pong

Living Room and the Entertainment Center contains books, puzzles board games, smart television, and a robust record collection.

Epic Game Room - shuffleboard, airhockey, foosball, ping pong, xbox, wii and much more.......

Kitchen and Dining Area - Perfect for family and friend gatherings. Our favorite is to play board games at the table while friends watch the Bruins, Patriot's or Red Sox games at the TV in the living room!

* Game Room, Linens, Quiet St, Central AC/Heat

4 bedrooms·2 baths

Harwich • Massachusetts

5(343 reviews)

$949.62 USD total for 3 nights

Oct 25 – 28, 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)

$954.59 USD total for 3 nights

Oct 24 – 27, 2026

Welcome to Katama Delight of Martha's Vineyard

South facing sunny balconies and deck

Welcoming entry to our home, laundry area enclosed by glass doors (adjacent to the kitchen)

Cathedral ceiling great room; a bright and airy space with plentiful seating

Spacious and bright cathedral ceiling great room; sliding door to deck, lawn and garden

Katama Delight of Martha's Vineyard

4 bedrooms·3 baths

Edgartown • Massachusetts

$13,596.80 USD total for 7 nights

Oct 21 – 28, 2026

View of the Property

Berkshire vacation rental in a 10,000 acres forest

3 bedrooms·2 baths

Plainfield • Massachusetts

4.85(242 reviews)

$1,159.93 USD total for 3 nights

Oct 22 – 25, 2026

Private deck, facing side street.

Front of building. Our unit is the whole third floor.

Spacious fully equipped eat-in kitchen

Living room facing the bay

Lovely, West End, Water Views, Spacious!

2 bedrooms·1 bath

Provincetown • Massachusetts

4.95(83 reviews)

$1,533.75 USD total for 3 nights

Oct 25 – 28, 2026

Welcome! The home has been family owned & loved since 1962. Lots of great memories have been shared here. I look forward to hosting you while you create your own special memories. Quick stroll to the

The popular West Island Town Beach is resident only BUT a beach pass comes with your reservation. Enjoy the quiet surf, views of the Elizabeth Islands, watch kite surfing, fishing boats, pleasure boat

Off Sconticut Neck, which is a pennisula, and within a short walking or driving distance are tiny beaches for your sunrise or sunset viewing.

Off Sconticut Neck, which is a pennisula, and within a short walking or driving distance are tiny beaches for your sunrise or sunset viewing.

Off Sconticut Neck, which is a pennisula, and within a short walking or driving distance are tiny beaches for your sunrise or sunset viewing.

Warm & Sunny All Year Round. Come Visit!

4 bedrooms·2 baths

Fairhaven • Massachusetts

4.73(75 reviews)

$1,032.75 USD total for 3 nights

Nov 8 – 11, 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

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)

Relaxing porch furniture invites you to unwind in the midst of nature's spectacle. Sunset drenching the waterfront in warm hues, casting a golden glow. Enjoy a refreshing beverage by the water's edge as the sun bids adieu for today.

Beachfront/ Pool / Hottub/ Sauna & Panoramic views

View of the sun as it rises over The Heart of Somerset. Imagine witnessing this beauty with a cup of something warm and delicious in the morning.

Assorted coffees, teas, and Hot chocolate are all offered.

Pool with Waterfront view. Life jackets are available for non swimmers.

Patio furniture for wrap around deck facing the water. 2 love seats, 2 rocker chairs,4 chairs, 2 tables, 1 bistro set. (12 seats total)

Beachfront/ Pool / Hottub/ Sauna & Panoramic views

4 bedrooms·2 baths

Somerset • Massachusetts

5(192 reviews)

$3,931.00 USD total for 3 nights

Oct 19 – 22, 2026

Falmouth Heights Cottage

Falmouth Heights Beach

Fenced yard for dogs, kids, and family parties

Falmouth Heights Cottage ~ Cape Cod

3 bedrooms·2 baths

Falmouth • Massachusetts

5(68 reviews)

$3,116.47 USD total for 7 nights

Oct 19 – 26, 2026

7 person Artesian Grand Cayman hot tub with all the bells and whistles.

The living room has a gas fireplace, smart TV, and the couch can pull out for an extra bed for large groups.

The walk-out basement has a large screen smart TV, shuffleboard, magnetic dart board, pull-out couch, an ottoman that folds out into a single bed, a woodstove, and it all leads out to the hot tub. Free firewood is just outside the door.

Great spot to have your morning coffee and catch the morning sun.

Master bedroom with flat-screen smart TV, private bathroom including bathtub and shower, closet space, dressers, an LED wall mount fireplace, and a wall unit minisplit system for heating and cooling.

The Meadows House @ Otis Ridge w/ 7-person hot tub

3 bedrooms·2 baths

Otis • Massachusetts

4.84(204 reviews)

$964.45 USD $869.95 USD total for 3 nights

Oct 19 – 22, 2026

Cape Cod Classic Cottage Near Forest Beach image 1

Cape Cod Classic Cottage Near Forest Beach image 2

Cape Cod Classic Cottage Near Forest Beach image 3

Cape Cod Classic Cottage Near Forest Beach image 4

Cape Cod Classic Cottage Near Forest Beach image 5

Cape Cod Classic Cottage Near Forest Beach

2 bedrooms·1 bath

Chatham • Massachusetts

4.93(197 reviews)

$1,245.34 USD total for 3 nights

Oct 19 – 22, 2026

Bright, Spacious Bedroom

Bright and spacious room, comfy bed.

Cape Ann sunset (up the road at Plum Cove)

Quirky, Bright, Spacious Private Room Near Water

1 bedroom·1 bath

Gloucester • Massachusetts

5(17 reviews)

$552.00 USD total for 3 nights

Oct 22 – 25, 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

Gorgeous Sandy Priscilla Beach on Cape Cod Bay

Front view of Decks2Sea in Priscilla Beach

Front view of Decks2Sea in Priscilla Beach

Large living room with 60" Smart TV and custom leather sofa with Queen Pull out

Decks2Sea

4 bedrooms·2½ baths

Plymouth • Massachusetts

5(201 reviews)

$4,796.60 USD total for 3 nights

Oct 19 – 22, 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

Beautiful Home Close to National Seashore Beaches!

Well-appointed kitchen is bright and welcoming

Decor is clean, cozy, and calming for a pleasant time away!

Plenty of comfortable seats for the family to gather and relax.

Comfortable and calming first floor bedroom with queen bed.

Beautiful Home Close to National Seashore Beaches!

4 bedrooms·2½ baths

Eastham • Massachusetts

$1,265.06 USD total for 3 nights

Oct 19 – 22, 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

Hygge House on Richmond Pond

Hygge House on Richmond Pond

Hygge House on Richmond Pond

Hygge House on Richmond Pond

Hygge House on Richmond Pond

Hygge House on Richmond Pond

3 bedrooms·2 baths

Richmond • Massachusetts

4.95(62 reviews)

$1,701.67 USD total for 3 nights

Oct 20 – 23, 2026

Seas The Day image 1

Seas The Day image 2

fully stocked kitchen with microwave, dishwasher, keurig coffeemaker, toaster, blender, etc.

living room with cable TV

sunroom with washer/dryer.

Seas The Day

2 bedrooms·1 bath

Wareham • Massachusetts

4.92(66 reviews)

$1,230.00 USD total for 4 nights

Jun 10 – 14, 2027

Comfortable leather couch and two captains chairs

Barn Doors open to Bedroom

Lots of Sunlight. Great views of beautiful back yard

Eat In Kitchen dining table

Yachtsman Suite

1 bedroom·1 bath

Marblehead • Massachusetts

4.89(35 reviews)

$1,887.04 USD total for 3 nights

Oct 23 – 26, 2026