Chatham, MA, USA Vacation Rentals

United States Massachusetts Orleans vacation rental compare prices direct by owner 164412

Spacious Game Room Close to Nauset Beach!

5.0 (68)

4 Bedrooms • 12 Guests

$1,166 avg/night

United States Massachusetts Orleans vacation rental compare prices direct by owner 9368895

Luxurious, Modern Walk to Water!

5.0 (68)

3 Bedrooms • 6 Guests

$604 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 25804796

Waterfront with Private Dock!

5.0 (39)

4 Bedrooms • 8 Guests

$772 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 12588688

Sunroom Expansive Patio Fenced Yard!

5.0 (58)

4 Bedrooms • 8 Guests

$751 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 27280411

Hot Tub, Game Room, Large Private Yard!

5.0 (61)

3 Bedrooms • 8 Guests

$700 avg/night

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United States Massachusetts Chatham vacation rental compare prices direct by owner 11396652

Beautifully Renovated w/ Access to Beach!

4.9 (101)

6 Bedrooms • 14 Guests

$844 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 2534404

Dreamy Water Views w/ Central AC

4.9 (69)

3 Bedrooms • 6 Guests

$765 avg/night

United States Massachusetts Chatham vacation rental compare prices direct by owner 9335602

1 Mile from Downtown Chatham Walk to Pier

4.9 (84)

4 Bedrooms • 10 Guests

$609 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 200202

Lovely Home Close to Bike Path and Beach!

4.9 (110)

3 Bedrooms • 9 Guests

$455 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 1370217

2-Min Walk to the Beach Dog Friendly!

4.9 (61)

3 Bedrooms • 4 Guests

$626 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 631217

Walk to Beach, Central AC!

4.9 (57)

4 Bedrooms • 8 Guests

$621 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 10173552

Heated Saltwater Pool Hot Tub!

4.9 (34)

4 Bedrooms • 8 Guests

$711 avg/night

United States Massachusetts Orleans vacation rental compare prices direct by owner 27300127

Fantastic Home by Eldridge Park!

4.9 (44)

3 Bedrooms • 6 Guests

$366 avg/night

United States Massachusetts Chatham vacation rental compare prices direct by owner 26550033

Gorgeous Home with Game Room Dog Welcome!

4.9 (57)

3 Bedrooms • 8 Guests

$627 avg/night

United States Massachusetts Chatham vacation rental compare prices direct by owner 1973978

On the Chatham Loop - 1 Min to the Beach!

4.9 (62)

5 Bedrooms • 8 Guests

$651 avg/night

United States Massachusetts Chatham vacation rental compare prices direct by owner 222987

Stellar Home with Hot Tub & Movie Room!

4.9 (126)

4 Bedrooms • 10 Guests

$875 avg/night

United States Massachusetts Chatham vacation rental compare prices direct by owner 209451

Game Room Walk to Nantucket Sound!

4.9 (101)

4 Bedrooms • 10 Guests

$491 avg/night

United States Massachusetts Chatham vacation rental compare prices direct by owner 2318317

5-Mins to Forest Beach Dog Friendly!

4.8 (65)

3 Bedrooms • 6 Guests

$602 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 10956865

4 Mins to Bayside Beaches!

4.8 (61)

5 Bedrooms • 10 Guests

$763 avg/night

United States Massachusetts Dennis vacation rental compare prices direct by owner 33504959

Antique Dennis getaway with firepit & EV charger,

4.8 (34)

5 Bedrooms • 11 Guests

$492 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 177929

Beautiful Spacious Family Retreat w/ Pool!

4.8 (44)

4 Bedrooms • 8 Guests

$683 avg/night

United States Massachusetts Orleans vacation rental compare prices direct by owner 32840209

Perfectly private location w/deeded beach access!

4.8 (34)

3 Bedrooms • 6 Guests

$534 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 24968581

Close to Nauset Beach!

4.8 (54)

2 Bedrooms • 4 Guests

$586 avg/night

United States Massachusetts Eastham vacation rental compare prices direct by owner 2596453

Quintessential Captain's House w/ Water Views!

4.8 (65)

5 Bedrooms • 11 Guests

$1,012 avg/night

United States Massachusetts Chatham vacation rental compare prices direct by owner 165820

15 Minute Walk to Pleasant Street Beach!

4.8 (95)

4 Bedrooms • 8 Guests

$502 avg/night

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