Holiday rentals near Chatham Drama Guild
We found 4,570 holiday rentals — enter your dates for availability
Find the perfect private holiday rental within close proximity to Chatham Drama Guild. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as parking and a fireplace. What you'll find is a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Chatham Drama Guild
Showing deals for:21 Nov - 28 Nov
Image gallery for Chatham 3 Bedroom/2 Bath Retreat
9.09.0 out of 10 rating
Wonderful
(46 reviews)
Chatham 3 Bedroom/2 Bath Retreat
Chatham, MA
15% off
Price is NZ$3,996
NZ$3,996
NZ$571 per night
includes taxes & fees
Image gallery for Steps to private Beach, Golf Course, AC, tandem Kayak for Guests
9.69.6 out of 10 rating
Exceptional
(25 reviews)
Steps to private Beach, Golf Course, AC, tandem Kayak for Guests
South Yarmouth, MA
7% off
Price is NZ$2,237
NZ$2,237
NZ$320 per night
includes taxes & fees
Image gallery for Clean and Quiet cottage 1/2 mile to Cooks Brook and Sunken Meadow Beach
1010 out of 10 rating
Exceptional
(74 reviews)
Clean and Quiet cottage 1/2 mile to Cooks Brook and Sunken Meadow Beach
Eastham, MA
7% off
Price is NZ$2,335
NZ$2,335
NZ$334 per night
includes taxes & fees
Image gallery for Renovated, modern Chatham beach house with lots of cozy charm
9.89.8 out of 10 rating
Exceptional
(36 reviews)
Renovated, modern Chatham beach house with lots of cozy charm
South Chatham, MA
7% off
Price is NZ$5,324
NZ$5,324
NZ$761 per night
includes taxes & fees
Image gallery for Families: Enjoy Harwich, Pool, Large Hot Tub & AC!
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Families: Enjoy Harwich, Pool, Large Hot Tub & AC!
Harwich, MA
8% off
Price is NZ$14,764
NZ$14,764
NZ$2,109 per night
includes taxes & fees
Image gallery for Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach
1010 out of 10 rating
Exceptional
(71 reviews)
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach
Orleans, MA
16% off
Price is NZ$17,807
NZ$17,807
NZ$2,544 per night
includes taxes & fees
Image gallery for Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf
1010 out of 10 rating
Exceptional
(27 reviews)
Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf
Brewster, MA
7% off
Price is NZ$7,669
NZ$7,669
NZ$1,096 per night
includes taxes & fees
Image gallery for Quintessential 2-bedroom Cape cottage with salt marsh views near Seagull Beach
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Quintessential 2-bedroom Cape cottage with salt marsh views near Seagull Beach
West Yarmouth, MA
8% off
Price is NZ$3,282
NZ$3,282
NZ$469 per night
includes taxes & fees
Image gallery for Classic Bayside cottage, Near Northside Beaches, Private, Close to Sesuit harbor
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Classic Bayside cottage, Near Northside Beaches, Private, Close to Sesuit harbor
East Dennis, MA
7% off
Price is NZ$3,359
NZ$3,359
NZ$480 per night
includes taxes & fees
Image gallery for Cozy Cape Cottage
9.09.0 out of 10 rating
Wonderful
(19 reviews)
Cozy Cape Cottage
Brewster, MA
8% off
Price is NZ$3,190
NZ$3,190
NZ$456 per night
includes taxes & fees
Image gallery for Come enjoy Orleans and Chatham
1010 out of 10 rating
Exceptional
(17 reviews)
Come enjoy Orleans and Chatham
Orleans, MA
8% off
Price is NZ$3,878
NZ$3,878
NZ$554 per night
includes taxes & fees
Image gallery for Amazing location! Quiet, picturesque neighborhood!
1010 out of 10 rating
Exceptional
(112 reviews)
Amazing location! Quiet, picturesque neighborhood!
Orleans, MA
7% off
Price is NZ$3,718
NZ$3,718
NZ$531 per night
includes taxes & fees
Image gallery for Cute Cottage on Bass River in West Dennis
9.69.6 out of 10 rating
Exceptional
(50 reviews)
Cute Cottage on Bass River in West Dennis
West Dennis, MA
7% off
Price is NZ$2,991
NZ$2,991
NZ$427 per night
includes taxes & fees
Image gallery for Big House in Heart of Cape. Close to Everything!
1010 out of 10 rating
Exceptional
(111 reviews)
Big House in Heart of Cape. Close to Everything!
South Dennis, MA
8% off
Price is NZ$3,955
NZ$3,955
NZ$565 per night
includes taxes & fees
Image gallery for New, dog-friendly 5-bed home. Steps to Keyes Beach, Main Street, and Harbor!
1010 out of 10 rating
Exceptional
(148 reviews)
New, dog-friendly 5-bed home. Steps to Keyes Beach, Main Street, and Harbor!
Hyannis, MA
7% off
Price is NZ$6,629
NZ$6,629
NZ$947 per night
includes taxes & fees
Image gallery for Waterfront, Amazing Sunsets, Dock, Fishing and a Small Beach, 1 Bedroom Sleeps 3
9.09.0 out of 10 rating
Wonderful
(79 reviews)
Waterfront, Amazing Sunsets, Dock, Fishing and a Small Beach, 1 Bedroom Sleeps 3
West Dennis, MA
8% off
Price is NZ$3,331
NZ$3,331
NZ$476 per night
includes taxes & fees
Image gallery for Cape Cod Pond Cottage
8.88.8 out of 10 rating
Excellent
(33 reviews)
Cape Cod Pond Cottage
Eastham, MA
8% off
Price is NZ$2,795
NZ$2,795
NZ$399 per night
includes taxes & fees
Image gallery for Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
1010 out of 10 rating
Exceptional
(22 reviews)
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
South Chatham, MA
15% off
Price is NZ$5,020
NZ$5,020
NZ$717 per night
includes taxes & fees
Image gallery for Family Friendly Mid CapeHome•Close to all Beaches• Sleeps 6 •Steps to Kelly Bay
9.69.6 out of 10 rating
Exceptional
(68 reviews)
Family Friendly Mid CapeHome•Close to all Beaches• Sleeps 6 •Steps to Kelly Bay
South Dennis, MA
7% off
Price is NZ$3,841
NZ$3,841
NZ$549 per night
includes taxes & fees
Image gallery for Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
1010 out of 10 rating
Exceptional
(12 reviews)
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
Chatham, MA
7% off
Price is NZ$4,641
NZ$4,641
NZ$663 per night
includes taxes & fees
Image gallery for Chatham Beach Chic 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
1010 out of 10 rating
Exceptional
(77 reviews)
Chatham Beach Chic 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
South Chatham, MA
8% off
Price is NZ$7,039
NZ$7,039
NZ$1,006 per night
includes taxes & fees
Image gallery for VILLA at Endicott Village GOLF PRIVILEGES AND VIEW Ocean Edge.LINENS PROVIDED
9.89.8 out of 10 rating
Exceptional
(74 reviews)
VILLA at Endicott Village GOLF PRIVILEGES AND VIEW Ocean Edge.LINENS PROVIDED
Brewster, MA
8% off
Price is NZ$6,451
NZ$6,451
NZ$922 per night
includes taxes & fees
Image gallery for Spacious 3 bedroom ranch close to beaches mall and restaurants. Great Location.
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Spacious 3 bedroom ranch close to beaches mall and restaurants. Great Location.
West Yarmouth, MA
7% off
Price is NZ$4,728
NZ$4,728
NZ$675 per night
includes taxes & fees
Image gallery for Chatham's Best Views-Harbor & Atlantic; On the Beach 4 Kayaks, 2 SUP's, 5 chairs
1010 out of 10 rating
Exceptional
(63 reviews)
Chatham's Best Views-Harbor & Atlantic; On the Beach 4 Kayaks, 2 SUP's, 5 chairs
North Chatham, MA
8% off
Price is NZ$12,629
NZ$12,629
NZ$1,804 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chatham Drama Guild
Convenient to all amenities and beaches in Chatham
Sleeps 2 · 1 bathroom
1010 out of 10
Exceptionalexceptional
188 reviews(188 reviews)
Edgewater Beach Resort, a VRI resort
Sleeps 4 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
282 reviews(282 reviews)
Holly Tree Resort
Sleeps 4 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
347 reviews(347 reviews)
All Seasons Resort
Sleeps 4 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
50 reviews(50 reviews)
LOCATION! Cabin sleeps3, POOL, 1 mile to OCEAN, Kitchen/Grill, Pet ok, Parking
Sleeps 3 · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
42 reviews(42 reviews)
Luxury 9 BR Home with Heated Pool in Downtown Chatham
Sleeps 21 · 9 bedrooms · 9+ bathrooms
1010 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value