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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: 22

Chatham

WATERVIEWS! 4 min drive to Hardings Beach!
6BR
4 ½ baths
Sleeps 17

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

Contact: Kibibi, Property ID: 4564

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

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

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.

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

Ridgevale-Walk to Beach-pets considered-spacious home
4BR
2 baths
Sleeps 9

This house is available as a winter rental from late September 2023 to mid May 2024, $1,595 per month plus utilities.

Contact: Paul K. McGrath, Property ID: 4560

Chatham Cottage < 1 mile to beach; 2 BR with Huge Loft
3BR
1 bath
Sleeps 8

Would consider monthly winter long term rental November - April (5000/mo)

Contact: Frank, Property ID: 35968

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

Ocean Side of Shore Road, walk to Town and Beaches
4BR
3 baths
Sleeps 6

No longer term winter rentals available

Contact: Robert Stevens, Property ID: 21315

3BR nr Hardings Beach, 5 min walk Oyster River,see reviews!
3BR
2 baths
Sleeps 6

Available as a winter rental end of October to mid May. $1200-1500/ month plus utilities and security deposit.

Contact: Bob Sneden, Property ID: 23722

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

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

3 Bedroom Chatham Cottage - Easy walk to Harding Beach!
3BR
1 bath
Sleeps 6

Wonderful location for OCTOBER - MAY long term rental available. Dates can be flexible. Please contact owner for details

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

Now With Central AC! Screened In Porch Too!
3BR
2 baths
Sleeps 6

There are no long term rentals for this property.

Contact: Alex, Property ID: 7862

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

Murray's Cottage: Central AC & steps from Rail Trail
3BR
2 baths
Sleeps 6

Long term winter rentals are considered, please send a request if interested.

Contact: Yulia, Property ID: 33894

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

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

5 overnight (6 Beach Guests.) 3 car overnight max. LIMIT Strictly enforced. External only - 2 Blink outside surveillance units secure the hom...

Contact: Gregory Johnson, Property ID: 1695

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

Charming Chatham Village Cottage
2BR
1 bath
Sleeps 4

Sorry, this Cottage is only available for short term rentals; 1-2 weeks maximum. Have to spread the love!

Contact: Margie Downes, Property ID: 8815

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