Holiday rentals near Chatham Drama Guild
We found 4,581 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 AU$3,609
AU$3,609
AU$516 nightly
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 AU$2,019
AU$2,019
AU$288 nightly
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 AU$4,808
AU$4,808
AU$687 nightly
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 AU$13,232
AU$13,232
AU$1,890 nightly
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
(70 reviews)
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach
Orleans, MA
16% off
Price is AU$16,166
AU$16,166
AU$2,309 nightly
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 AU$2,105
AU$2,105
AU$301 nightly
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 AU$6,901
AU$6,901
AU$986 nightly
Includes taxes & fees
Image gallery for Dream Beach House on Mayo Beach Wellfleet Cape Cod
1010 out of 10 rating
Exceptional
(16 reviews)
Dream Beach House on Mayo Beach Wellfleet Cape Cod
Wellfleet, MA
8% off
Price is AU$18,523
AU$18,523
AU$2,646 nightly
Includes taxes & fees
Image gallery for Private Cape Rental 1 Mile from the Beach!
1010 out of 10 rating
Exceptional
(22 reviews)
Private Cape Rental 1 Mile from the Beach!
East Dennis, MA
7% off
Price is AU$7,574
AU$7,574
AU$1,082 nightly
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 AU$3,031
AU$3,031
AU$433 nightly
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 AU$2,879
AU$2,879
AU$411 nightly
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 AU$3,500
AU$3,500
AU$500 nightly
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 AU$3,356
AU$3,356
AU$479 nightly
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 AU$3,570
AU$3,570
AU$510 nightly
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 AU$2,701
AU$2,701
AU$386 nightly
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 AU$6,026
AU$6,026
AU$861 nightly
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 AU$3,006
AU$3,006
AU$429 nightly
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
(21 reviews)
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
South Chatham, MA
15% off
Price is AU$4,533
AU$4,533
AU$648 nightly
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 AU$6,349
AU$6,349
AU$907 nightly
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 AU$3,469
AU$3,469
AU$496 nightly
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 AU$4,191
AU$4,191
AU$599 nightly
Includes taxes & fees
Image gallery for Private Cape Cod Cottage. Walk to Ellis Landing Beach!
1010 out of 10 rating
Exceptional
(34 reviews)
Private Cape Cod Cottage. Walk to Ellis Landing Beach!
Brewster, MA
8% off
Price is AU$3,198
AU$3,198
AU$457 nightly
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 AU$5,824
AU$5,824
AU$832 nightly
Includes taxes & fees
Image gallery for Spacious 3 bedroom ranch close to beaches mall and restaurants. Great Location.
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Spacious 3 bedroom ranch close to beaches mall and restaurants. Great Location.
West Yarmouth, MA
7% off
Price is AU$4,271
AU$4,271
AU$610 nightly
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
187 reviews(187 reviews)
Edgewater Beach Resort, a VRI resort
Sleeps 4 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
281 reviews(281 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
36 reviews(36 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