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Long-Term Vacation Rentals in Chatham

Rental homes are available for an extended stay of a month or more at a time. While some rentals by owner will be available for long-term stays during the summer or year-round, majority are available during the off-season (fall, winter and spring). Monthly prices may vary depending on the number in your party and length of stay.

Rentals are listed by location, sleeping capacity, and number of bedrooms.

# of Rentals: 31

Chatham

20% Discount until May 2021, BOOK for Wedding season 2022!
6BR
4 ½ baths
Sleeps 20

Available monthly from October - April 30. Six person occupancy. Three cars.

Contact: Kibibi, Property ID: 4564

The ''Coastal Living'' house, the ideal beach house design!
6BR
4 baths
Sleeps 15

Off season considered and negotiable

Contact: Andrew, Property ID: 33703

Walk to Town, Beaches, & Park. We provide a solid product.
5BR
4 baths
Sleeps 15

Copy and Paste these links, so you can see more photos of the house and some from walks I went on in May 2020. https://www.dropbox.com/sh/hup47skbl...

Contact: Arlene and Matthew, Property ID: 32710

Ridgevale-Walk to Beach-pets considered-spacious home
4BR
2 baths
Sleeps 11

This house is available as a winter rental from late September 2021 to mid May 2022 for $1,200 per month plus utilities.

Contact: Paul K. McGrath, Property ID: 4560

Chatham Walk to Hardings Beach Spectacular Oceanview House
5BR
4 ½ baths
Sleeps 10

November, December, January, February, March, April. $6500 per month.

Contact: Wendy Gruenberg, Property ID: 16695

Beautiful Family Home, Walk to Beach, Ball Game and Town
4BR
2 baths
Sleeps 10

In town of Chatham! Great family home! 4 bedrooms, 2 baths. Fully furnished including linens. Located near schools,town and park. Available for winter...

Contact: Lauren Cardillo, Property ID: 19554

True Waterfront 4 Bedrooms, 4 Acres on Nantucket Sound
4BR
2 baths
Sleeps 10

Possible. $3500 per month plus utilities

Contact: Harvey Ross, Property ID: 9648

Pool table,Ping Pong, Sun Room,4 BR,sleeps 10
4BR
2 baths
Sleeps 10

Columbus Day to Mid May $1250/mo plus utilities.

Contact: Bob Sneden, Property ID: 23543

Waterfront home with spacious living areas and water views
4BR
3 ½ baths
Sleeps 10

We welcome long-term rentals at a discounted rate to interested parties. Off season rates apply between October and April. $3,500/ week non-negotiable...

Contact: Stephen, Property ID: 16212

Chatham Beach Chic 5 STAR Family retreat-5 min walk to Beach
3BR
2 baths
Sleeps 10

Tennis court, basketball hoop and children climbing gym available to our guests.

Contact: John Muldoon, Property ID: 24757

Lucky Ducks - Contemporary Cape with AC in North Chatham
4BR
2 baths
Sleeps 9

Open to winter long-term rentals December thru April. Two month minimum.

Contact: Christina, Property ID: 32966

Wildlife Lovers Salt Pond Perch.An Authentic Cape Experience
4BR
2 baths
Sleeps 8

Monthly or longer rental available from October through April at $1,200 a month.

Contact: Sylvia, Property ID: 31092

Sunny and Immaculate, Steps from Ridgevale Beach
3BR
2 baths
Sleeps 7

This home is available for month or longer long term off-season rentals. Please contact us for more information.

Contact: Lisa, Property ID: 33933

Charming Chatham-Walking Distance to Beaches and Downtown
3BR
2 baths
Sleeps 7

Chatham close to town, tennis courts and bike path. Late September 2020 to mid May 2021 for $975/month depending on party size and length of stay. Ut...

Contact: Maureen and John Hillier, Property ID: 14456

Newly Restored Cottage
3BR
2 ½ baths
Sleeps 6

The only months available for long term rents are Nov., Dec. Jan. Feb. March, April minimum rent $1600 month plus utilities

Contact: Joyce Anderson, Property ID: 25053

Perfect Chatham Beach Cottage - Easy Walk to Hardings Beach!
3BR
1 bath
Sleeps 6

Wonderful location for OCTOBER - MAY long term rental available at $1,200/ month plus utilities. Please contact owner

Contact: Jim, Property ID: 28721

LOCATION AND VIEW! Waterfront Cottage In Town
3BR
1 ½ bath
Sleeps 6

We would consider a 6 month rental (starting Oct/Nov). $20,000

Contact: Erin, Property ID: 28980

Chatham Cottage with Ocean Views
3BR
1 bath
Sleeps 6

Winter rentals are available both short term and long term. Weekly rentals start $700 a week, plus cleaning fees.

Contact: Joann Perlo, Property ID: 29561

Value! Charming Chatham 3 Bedroom Home; Close to Town/Water
3BR
1 ½ bath
Sleeps 6

Sleeps 6 in 3 Bedrooms. Available approx November through May. $1400-$3500 monthly depending upon length of stay, plus utilities or $1250-1500 weekly....

Contact: Catherine Batcheller, Property ID: 20787

Traditional Cape Cod Cottage, Walk to Hardings Beach
3BR
1 bath
Sleeps 6

September to June: Contact owner for pricing, no utilities included.

Contact: Bruce Newcomb, Property ID: 24317

Great getaway!Walk to beach & pond & water-sports!
3BR
1 bath
Sleeps 6

Not available

Contact: Nancy, Property ID: 33418

Outermost Waterfront Chatham Home w/Wraparound Views & AC!
2BR
2 baths
Sleeps 6

Long-term off-season rental is considered on a monthly basis ($3500/mo), between November and April.

Contact: Sarah & Dave, Property ID: 33598

Cozy Chatham Condo
2BR
2 baths
Sleeps 6

Long term winter rentals are considered. All utilities must be paid by the tenant.

Contact: Susan Palmer, Property ID: 7710

Chatham's Best Views On Large Sandy Beach,4 Kayaks, 2 SUP's
3BR
3 ½ baths
Sleeps 5

5 overnight or Beach Guests. 3 car overnight max. LIMIT Strictly enforced. External only - 2 Blink outside surveillance units secure the home'...

Contact: Gregory Johnson, Property ID: 1695

The Atrium House, Waterfront with Interior Garden
3BR
1 ½ bath
Sleeps 5

Possible consideration for a month or so for adults only. We do not accept pets at this time.

Contact: Kim, Property ID: 28082

Oceanfront Holiday Shores, Seaside Cottage, South Chatham MA
2BR
1 bath
Sleeps 5

Available off season for $1000 per week April 21 - June 16 September 5 - Nov. 17

Contact: Pam Parsons, Property ID: 13850

New Listing! Picture Perfect, Pet Friendly Home
2BR
1 ½ bath
Sleeps 5

November to May for $3500 a month, depending on length of stay. Cable/Utilities included with a $250 gas heat allowance per month.

Contact: Laura, Property ID: 34584

Waterfront setting on Private Freshwater Pond
2BR
2 baths
Sleeps 4

We recognize and support working from home as a winter rental option for a single or professional couple during the pandemic. Also, perfect for a ret...

Contact: Kim, Property ID: 13085

Chatham Village cottage weekly summer rental 2nt off season
1BR
1 bath
Sleeps 3

The cottage is available in the off-season Oct. - May as a monthly rental for $1000/mo. All utilities included.

Contact: Carol, Property ID: 30589

Million Dollar Location - can sleep two adults + baby
1BR
1 bath
Sleeps 3

Potentially

Contact: Elizabeth, Property ID: 34242

Cozy Cottage
1BR
1 bath
Sleeps 2

Call to discuss

Contact: Jeff and Kelly Craugh, Property ID: 17464