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Vacation rentals in Orleans, Massachusetts, United States

Charming Family-Friendly, 3+ Bedroom, Farmhouse

Sunny kitchen with water filter on fridge and new stove in 2022. See other photos for close up of the new stove.

Charming Family-Friendly, 3+ Bedroom, Farmhouse

Bertazzoni gas range and electric oven installed in 2022 with superfast boil and pizza setting on the oven.

Sunny bright cook's kitchen is a delight to use. You'll find spices, gadgets, Kitchenaid mixer, blenders etc. New Bertazzoni gas range ‘22

Charming Family-Friendly, 3+ Bedroom, Farmhouse

4 bedrooms·2 baths

Orleans • Massachusetts

4.97(39 reviews)

$3,783.50 USD total for 4 nights

Oct 31 – Nov 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 31 – Nov 3, 2026

Brand New Luxury Home: Private Outdoor Oasis, Hot Tub, Sauna

5 bedrooms·3 baths

Eastham • Massachusetts

$2,901.52 USD $2,656.37 USD total for 3 nights

Oct 31 – Nov 3, 2026

Perfect Cape Escape ! image 1

Perfect Cape Escape ! image 2

Perfect Cape Escape ! image 3

Perfect Cape Escape ! image 4

Perfect Cape Escape ! image 5

Perfect Cape Escape !

3 bedrooms·2 baths

Harwich • Massachusetts

4.75(8 reviews)

$2,430.00 USD total for 4 nights

Oct 31 – Nov 4, 2026

PRIVATE BEACH Bay views image 1

Comfortable cottage with bay views on a private beach.

PRIVATE BEACH Bay views image 3

The view from your cottage. Bay views and Sunsets over the water.

Your private beach looking west

PRIVATE BEACH Bay views

2 bedrooms·1 bath

Brewster • Massachusetts

4.98(87 reviews)

$1,950.00 USD total for 3 nights

Nov 1 – 4, 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 31 – Nov 3, 2026

Well lit entry way.

Hot tub, deck and outdoor shower.

Cozy living room with sectional and recliner.

Harwich Port Get a Way. Bring your Boat!

Dining area with additional folding table and chairs

Harwich Port Get a Way. Bring your Boat!

5 bedrooms·3 baths

Harwich • Massachusetts

$5,600.00 USD total for 7 nights

Oct 31 – Nov 7, 2026

Luxury Getaway with Hot Tub!

Luxury Getaway with Hot Tub!

Luxury Getaway with Hot Tub!

Luxury Getaway with Hot Tub!

Luxury Getaway with Hot Tub!

Luxury Getaway with Hot Tub!

4 bedrooms·3 baths

Harwich • Massachusetts

$1,878.27 USD total for 3 nights

Oct 31 – Nov 3, 2026

Deck, Bbq Grill, & Porch

WALK to WELLFLEET’s INDIAN NECK BEACH

3 bedrooms·2 baths

Wellfleet • Massachusetts

$275/ night(excl. fees & taxes)

Beautiful, inviting, and classic but modern.

Chef's kitchen, fully equipped. Gas stove.

Comfortable communal dining.

Dining outdoors, either on the deck or at the firepit.

The Map House - Modern Wellfleet Vacation

3 bedrooms·2 baths

Wellfleet • Massachusetts

5(3 reviews)

$1,230.34 USD total for 3 nights

Nov 1 – 4, 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)

$935.40 USD total for 3 nights

Nov 2 – 5, 2026

Back of house, private deck & wooded property

Teak dining table with umbrella

Gorgeous Cape with Deck Close to Ponds and Ocean

3 bedrooms·2 baths

Wellfleet • Massachusetts

$3,614.63 USD total for 7 nights

Oct 31 – Nov 7, 2026

2 minute Walk to beach and town (from our quiet dead-end road) through charming "Campground" neighborhood

Easy stroll to the warm waters of Nantucket Sound beach

Awesome beach at the end of the street!

Pottery Barn Kitchen table seats six

The Breakfast bar raea seats 4

Harwichport Walk to Beach & Town

4 bedrooms·2½ baths

Harwich • Massachusetts

5(6 reviews)

$2,806.48 USD total for 3 nights

Oct 31 – Nov 3, 2026

Thompson House Cape Cod

Thompson House Cape Cod

Thompson House Cape Cod

Thompson House Cape Cod

Thompson House Cape Cod

2 bedrooms·1 bath

Yarmouth • Massachusetts

3(2 reviews)

$3,815.69 USD total for 7 nights

Oct 31 – Nov 7, 2026

Coastal Cape Cod Cottage Charm. Unwind after a long day at the beach and sightseeing - comfortable seating and smart TV.

Thoughtfully curated with amenities that will leave you feeling relaxed with everything you need and more!

Dining for 4 both inside and out (picnic table with umbrella) with cooking supplies for making meals on the stove, in the oven or on the grill!

Beach Grass Cottage has been totally remodeled with guest comfort in mind!

Kitchen has stove, oven, microwave, fridge/freezer, coffee maker, and kitchen items to cook either inside our out!

Cape Cod Beachgrass Cottage - Walk to Beach+ !!

2 bedrooms·1 bath

Dennis • Massachusetts

5(6 reviews)

$1,001.44 USD total for 3 nights

Dec 23 – 26, 2026

Living room with plenty of windows/light! Smart TV and some games/books.

Smart TV in the living room. Please bring your own passwords.

Cape Cod Romantic Getaway *Walk to Beach, Fire Pit

Bedroom with Queen bed, charging ports, dressers Smart TV and electric wall fireplace (not shown). We also changed out the fabric headboard to non-fabric.

Full bathroom with shower (there’s also an outdoor shower).

Cape Cod Romantic Getaway *Walk to Beach, Fire Pit

1 bedroom·1 bath

Dennis • Massachusetts

$2,203.17 USD total for 7 nights

Dec 23 – 30, 2026

Cozy Coastal Retreat West Dennis - 13

Cozy Coastal Retreat West Dennis - 13

Cozy Coastal Retreat West Dennis - 13

Cozy Coastal Retreat West Dennis - 13

Cozy Coastal Retreat West Dennis - 13

Cozy Coastal Retreat West Dennis - 13

3 bedrooms·1 bath

Dennis • Massachusetts

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15

3 bedrooms·1 bath

Dennis • Massachusetts

$2,058.66 USD total for 4 nights

Apr 1 – 5, 2027

Spacious Retreat for Relaxation

Spacious Retreat for Relaxation

Spacious Retreat for Relaxation

Spacious Retreat for Relaxation

Spacious Retreat for Relaxation

Spacious Retreat for Relaxation

4 bedrooms·3 baths

Yarmouth • Massachusetts

$880.00 USD total for 3 nights

Nov 22 – 25, 2026

Living Room
(Game Cabinet; Dogs Beds on Top)

'The Whale's Tail' ~ Dogs Welcome

3 bedrooms·2 baths

Yarmouth • Massachusetts

5(1 review)

$1,100.00 USD total for 3 nights

Oct 31 – Nov 3, 2026

Ample backyard seating

Outdoor patio with seating area

Swan Pond is located within 0.5 miles from the house or 10 minutes walk!

Front of the house with a driveway that accommodates 2 cars

Kids are having so much fun at Swan Pond. 10 mins walk from the house.

Great Location, Yarmouth Beaches, Fenced-in yard!

2 bedrooms·1 bath

Yarmouth • Massachusetts

$180/ night(excl. fees & taxes)

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

Fully Renovated 3-Bedrooms 2-Baths W/En-suite.

3 bedrooms·2 baths

Yarmouth • Massachusetts

$250/ night(excl. fees & taxes)

Cape Cod Coastal Cottage Charm meets modern conveniences. Indulge yourself!

Kitchen has been completely redone and is fully stocked. Granite countertops, gas stove/oven, brisker, toaster oven, coffee maker, Keurig, french press, coffee bean grinder, grilling tools, pots/pans, basic spices, non-stick spray, etc.

Cape Cod Coastal Cottage Decor - be tastefully surrounded with the reason you are here! The Beach!

Cape Cod Coastal Cottage Decor - be tastefully surrounded with the reason you are here! The Beach!

Enclosed outdoor shower with hot/cold water.

Cape Cod Seagrass Cottage: Walk to Beach+Amenities

2 bedrooms·1 bath

Yarmouth • Massachusetts

5(1 review)

$3,422.06 USD total for 7 nights

Dec 23 – 30, 2026

WaterAccess 5-Bed 2-Bath Retreat

WaterAccess 5-Bed 2-Bath Retreat

WaterAccess 5-Bed 2-Bath Retreat

WaterAccess 5-Bed 2-Bath Retreat

WaterAccess 5-Bed 2-Bath Retreat

WaterAccess 5-Bed 2-Bath Retreat

5 bedrooms·2 baths

Barnstable • Massachusetts

$3,356.94 USD total for 4 nights

Apr 1 – 5, 2027