East Orleans

Browse Vacation Rentals

Private Association Beach Access, NEW to rentals (2418)

4.00 (1)

Dennis Port, Massachusetts

3 bedrooms•1 baths

Cozy Home in Quiet & Convenient Area (1140)

4.50 (4)

Orleans, Massachusetts

3 bedrooms•2 baths

$1,065for 3 nights•Nov 22 – Nov 25

NEW for 2026! Views of Cotuit Bay, pool, dock, beach area & hot tub RPMS156

Cotuit, Massachusetts

7 bedrooms•5.5 baths

Home on Great Island overlooking Nantucket Sound with Private Beach (1199)

4.60 (5)

West Yarmouth, Massachusetts

4 bedrooms•3 baths

$5,202for 7 nights•Nov 1 – Nov 8

Close to Beach, Harbor Out Front, Village Around the Corner! RPAM122

Harwich Port, Massachusetts

4 bedrooms•3.5 baths

Lovely home with heated pool, dock and the best views! RPMS158

Chatham, Massachusetts

6 bedrooms•4 baths

$25,643for 7 nights•Oct 31 – Nov 7

Your Private Harwich Resort w/ Heated Pool and Game Room RPAM118

Harwich, Massachusetts

4 bedrooms•2.5 baths

$2,823for 4 nights•Oct 30 – Nov 3

Iconic Brownie's Cabin, close to everything! (CS0046)

Wellfleet, Massachusetts

2 bedrooms•1 baths

Year-Round White Mountain Getaway at The Lodge RPAM127

Lincoln, New Hampshire

1 bedroom•1 baths

$1,019for 3 nights•Oct 30 – Nov 2

Wellfleet 2BR Retreat – Walk to Bay & Kayak! RPMC007

Wellfleet, Massachusetts

2 bedrooms•1.5 baths

Beach front, desirable Indian Neck! CS0048

Wellfleet, Massachusetts

4 bedrooms•2 baths

Offers ocean Views and Access & is Great for All Ages! (2249)

4.89 (9)

West Yarmouth, Massachusetts

3 bedrooms•3 baths

$2,198for 3 nights•Nov 8 – Nov 11

Enjoy your own private pool in Chatham! (2252)

5.00 (2)

South Chatham, Massachusetts

4 bedrooms•2.5 baths

$2,799for 3 nights•Dec 17 – Dec 20

Cottage with Views of the Atlantic Ocean (1221)

4.59 (22)

Wellfleet, Massachusetts

3 bedrooms•1 baths

$2,150for 7 nights•Nov 2 – Nov 9

A Rare First Offering in Chatham | Morris Island New for 2027!

Chatham, Massachusetts

5 bedrooms•4.5 baths

Plan Ahead

Everything you need for your stay

Browse Vendors