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Long-Term Vacation Rentals on Lower Cape Cod

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: 86

Brewster

Beautiful Home Close to Beaches, Sesuit Harbor & Golf
6BR
3 baths
Sleeps 13

'October to May for $3,000 per month, depending on party size and length of stay. Includes utilities.'

Contact: Gerry or Cindy, Property ID: 19604

Sheep Pond Escape - 5 bedroom with private beach
5BR
3 baths
Sleeps 12

1-week rate: $4,000 (includes cleaning fee) 2-week rate: $6,500 (includes cleaning fee) 4-week rate: $10,000 (includes cleaning fee)

Contact: Talia, Property ID: 34024

Renovated Brewster Beach House + Cottage
4BR
3 baths
Sleeps 12

Longer rentals of this newly renovated and private property in Brewster are available on a case-by-case basis. Please inquire for details. Generally...

Contact: Christine and Steve, Property ID: 33519

Gorgeous 4 Bedroom, 3.5 Bath Home w/AC in Brewster
4BR
3 ½ baths
Sleeps 12

We would be interested in a Long Term Winter tenant.

Contact: Kevin and Erin, Property ID: 33835

Stars Align Near Pleasant Bay
4BR
2 baths
Sleeps 10

Available January-March, $7000 a month +utilities

Contact: Elise Costa, Property ID: 36106

Sheep's Pond,Open Concept Family Home, Plenty of Fun
4BR
2 baths
Sleeps 10

Longer term renters are avaliable Oct through April.

Contact: Annmarie, Property ID: 30493

Charming Cottage and Glamping Bunkhouse Steps From The Beach
3BR
1 bath
Sleeps 10

The long term rental calendar is open for December 15 2022-April 15 2023.

Contact: Carole , Property ID: 31348

Brewster's Best Private Bay Beach Getaway - monthly rentals
3BR
2 baths
Sleeps 10

We would consider a winter rental if one was to be remodeling or relocating, must be out by May 1st

Contact: Roger Gallagher, Property ID: 19762

Family Friendly Home at Cobbs Pond/Cape Cod Bay in Brewster
4BR
3 baths
Sleeps 8

Long term can be done in off season

Contact: Jenn, Property ID: 19423

Private Beach Access, Great Family Get Away
4BR
2 baths
Sleeps 8

Some longer term rental is available. Please contact owner for specific information

Contact: Nick, Property ID: 30572

Brewster Mountain Retreat (Blueberry Pond)
3BR
2 baths
Sleeps 8

Available from December - May for multi month rental. Price is $2,500/month.

Contact: Eric, Property ID: 33279

Luxury Waterfront Oasis on Private Sunset Beach
3BR
2 baths
Sleeps 8

$2500-$4000

Contact: James and Janet, Property ID: 33328

The Mink Shell - 5 Min Walk to TWO Bay Beaches!!
3BR
2 baths
Sleeps 8

If looking to retire on the Cape or just wintering and you need a wonderful place to stay while you find your dream home, try ours for the season! Ava...

Contact: John, Martha, Elly and little Olivia, Property ID: 5843

Renovated Coastal Farmhouse at Greenland Pond
3BR
2 baths
Sleeps 8

Open to consideration between November and April. Monthly rentals begin at $3500 and include utilities.

Contact: Christine and Steve, Property ID: 35643

Escape to the Cape
3BR
3 baths
Sleeps 6

Long-term rental considered September 2021 - May 2022. Monthly rentals vary for the off season months starting at $4,000.

Contact: Margaret, Property ID: 34624

Birdwatcher's Delight
3BR
1 ½ bath
Sleeps 6

Available upon request. For two months or more, monthly rent is $2,400 in the winter months (December, January, February, March); $3,800 / month in sp...

Contact: Mary, Property ID: 12150

Well-appointed Home Steps from Private Sunset Beach
3BR
1 ½ bath
Sleeps 6

$2500-$4000

Contact: James and Janet, Property ID: 25423

Lovely Beach Cottage, Grassy Yard, Walk to Bay!
3BR
1 ½ bath
Sleeps 6

For the right person or couple, we are open to discussing winter rentals from October 15, 2022 through May 31, 2023. We charge $1850.00 per month plus...

Contact: Liz, Property ID: 29262

Perfect Cape Cottage
2BR
1 bath
Sleeps 6

***WINTER RENTAL AVAILABLE 2022-2023*** SEPTEMBER - JUNE...HURRY! WON'T LAST LONG :)

Contact: Jacqueline , Property ID: 32667

Charming 2 Bedroom near Breakwater Beach
2BR
1 bath
Sleeps 6

September 15 to May 31

Contact: John , Property ID: 23175

Private Beachfront sunset cottage on bluff . Bay views
2BR
1 bath
Sleeps 4

Winter rental available starting in Nov. - April $7000 a month.

Contact: Bruce or Rina , Property ID: 30177

Charming Beach Cottage Retreat - Walk to Paines Creek Beach
2BR
1 bath
Sleeps 4

Long Term Rental both Summer and Winter is an option and can be discussed based on month and availability.

Contact: Lou, Property ID: 36330

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

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

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

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

Harwich

Fabulous Lake Front Family Retreat
5BR
3 ½ baths
Sleeps 14

$3000/mo from October through May. If you're looking to relocate, trying to find your own piece of Cape Cod heaven but don't want to jump into a commi...

Contact: Susan Speight, Property ID: 12069

Charming 5 bedroom home, 2 master suites, affordable
5BR
2 baths
Sleeps 13

If interested, pls call to discuss 571 213 0800. Don't miss out on the summer at the Cape - off season rental also availabile as well as weekends! ...

Contact: Mary Anne Burke, Property ID: 15561

Great for 2 families, 2 masters both with their bathroom
4BR
3 baths
Sleeps 11

October through April; $3,000/month

Contact: Lori, Property ID: 21491

Waterfront 4 Bedroom 4 Bath Sleeps 10, Dock, Lake, & Kayaks!
4BR
4 baths
Sleeps 10

Quiet vacations in the winter, monthly rates $8000.

Contact: Greg Stone, Property ID: 13970

GAME ROOM, Wifi, Linens, Bikes, Quiet Street
4BR
2 baths
Sleeps 10

We are available for winter getaways for 28 days or less. Please contact us to inquire. Winter/Spring/Fall is a great time to visit the Cape!

Contact: Stacey, Property ID: 30468

Harwich Port Beach Home W/Ac Sleeps 10; 3/10 Mile To Beach
4BR
2 ½ baths
Sleeps 9

This house will be offered as 1-2 bedroom home during winter season from Nov - April for discount rate. and only open 1 to 2 for up to 2 occupancy. ...

Contact: Nina, Property ID: 31116

Charming South Harwich Cape With Ocean View & Walk 2 Beach
4BR
2 ½ baths
Sleeps 9

House is now booked to October 25, 2022, and then would be available to the right party from November to mid-May. Please contact me and tell me about...

Contact: Dennis Wiggins, Property ID: 5382

Outstanding Harwich Long Pond Family Home
4BR
2 baths
Sleeps 8

Fall and winter rentals are available from September through April. Pricing is from $1700-$1900 per month depending on the month of rental.

Contact: Norma Jean, Property ID: 22979

Brand new house, 150yards to Bank Street Beach, South of 28
3BR
2 ½ baths
Sleeps 8

This house is available for Winter Rental

Contact: Paul, Property ID: 13603

Happy Hours: Central AC & Walk to a Freshwater Beach
3BR
2 baths
Sleeps 8

Long term rentals available after Labor Day (September) until Memorial Day (May), $3400/month.

Contact: Tom and Dan Camarro, Property ID: 26783

Relaxing 3 BR Home in Quiet Neighborhood
3BR
2 ½ baths
Sleeps 8

Sept-May Offseason Rentals Considered ranging from $2200-2500/mo

Contact: Jason, Property ID: 33774

Family Home, Short Walk to Beach
3BR
2 baths
Sleeps 8

Lovely home available with one car garage for snow protection. Mid September through May.

Contact: Maura Sweeney, Property ID: 35462

Spacious Retreat with Backyard Oasis & Private Heated Pool
3BR
2 ½ baths
Sleeps 8

Contact us if interested

Contact: Nimra, Property ID: 35785

HarwichPort beach home, walk to Red River Beach, central air
3BR
2 baths
Sleeps 7

Long term rental already taken for the 12/15/22- 4/30/23 off season. Check back next year!

Contact: Laura and Jim, Property ID: 29274

''Reliance Retreat'' On ''Old Cape Cod,'' Newly Renovated
2BR
1 bath
Sleeps 6

Available Sept 15 to May 31 $1550/month includes utilities, basic cable and internet

Contact: Ron and Diana , Property ID: 31484

Two Bedroom with Loft Luxury Home
2BR
1 bath
Sleeps 5

This Luxury home is available for winter rental at $1800 per month . Minimum winter rental is 6 months.

Contact: Michael McNally or Chris Sage, Property ID: 22987

Sand Between Your Toes at Drangea Cottage Bank Street Beach
2BR
1 bath
Sleeps 4

$1,195.00 a month for 8 month lease, October through May, Start date negotiable, Furnished, W/D, includes heat. Tax Not Applicable. e-mail Ruth fo...

Contact: Ruth & Brad, Property ID: 9736

Spacious Cottage with Views of Herring River
2BR
1 bath
Sleeps 4

$1500/mth 0ct to june. plus utilities gas heat and electric

Contact: John B Hepburn, Property ID: 36387

Cozy in-town Harwich Port Condo
1BR
1 bath
Sleeps 3

Long term winter renters consider

Contact: David Brady, Property ID: 33804

Luxury One Bedroom Unit in Harwich Port Center
1BR
1 bath
Sleeps 3

Long term winter rental available for 1600.00 a month Includes all utilities, Gas, Electric, Cable. Minimum winter rental, 6 months.

Contact: Michael McNally or Chris Sage, Property ID: 22990

Orleans

Executive Waterfront Luxury Estate; Heated Pool; 6000 Sq.ft.
4BR
6 baths
Sleeps 16

Experience Cape Cod at this 6000 sq.ft Luxury Waterfront estate /w heated pool. Offers long-term rentals in July and August. Inquire for detail quote ...

Contact: Alex, Property ID: 14224

Stunning Property with Private Pool and Walk to Ocean Beach
6BR
4 ½ baths
Sleeps 12

Off season rentals are available. Pricing assumes renter is responsible for utilities. Pool will be closed and outdoor furniture will be stored in the...

Contact: Robert, Property ID: 31175

Nauset Beach House - Big, Beautiful, Views, Walk To Beach!
4BR
3 ½ baths
Sleeps 12

This home is available for winter rental between Oct 15-April 1. Obviously it is fully furnished. The amount of rent somewhat depends on the # of peop...

Contact: Kenneth, Property ID: 29075

Bright waterfront haven with AC and heavenly 100° views
4BR
3 ½ baths
Sleeps 10

The house is not available for long-term rentals. It is, however, available for bookings of up to 30 days, and Fall, Winter, and Spring guests appreci...

Contact: Andrew , Property ID: 31120

Beautiful Nauset Beach 4 Br Home, A/C, Wifi, Slp 12
4BR
3 baths
Sleeps 10

This home will be offered as a one or two bedroom home at winter season (from Jan -March) from $1300 ; Nov & Dec & April from $1800/mon plus all util...

Contact: Nina, Property ID: 9286

Unique & Charming Renovated Barn-Walk To Private Beach
4BR
3 ½ baths
Sleeps 10

No Winter rental 2020-2021

Contact: Kim, Property ID: 25214

Sunny, Charming, Kid-Friendly, Updated Farmhouse
3BR
2 ½ baths
Sleeps 10

Winter 2022/2023 is booked, but we are opening our cozy Orleans Farmhouse up for 2023/2024 winter rentals. You may rent any amount of time, ranging fr...

Contact: Carrie, Property ID: 29389

Water views, private waterfront, 2.7 mi. to Nauset Beach!
3BR
2 baths
Sleeps 10

October to May monthly rentals available. $3000 - $4000/mo. Please call Ruth ( 917-586-3753) or Phil (929-810-8068) to inquire further.

Contact: Ruth, Property ID: 20703

Renovated Beautiful Home-Dog Friendly! NEW KITCHEN!
4BR
2 baths
Sleeps 8

Please contact owner directly.

Contact: Judy , Property ID: 35920

3 BR Contemporary on Little Pleasant Bay with Private Beach
4BR
3 baths
Sleeps 8

Winter rental available starting February 2020, $3,500 per month with aggressive pricing for multiple months.

Contact: Bill, Property ID: 32875

Upscale East Orleans Home- 5 minutes to Nauset Beach!
3BR
2 baths
Sleeps 8

Please inquire

Contact: Mary Ella , Property ID: 33655

Summer 2022.Waiting List. Late Summer/Autumn Availability
3BR
3 baths
Sleeps 8

We are renting multiple weeks throughout the year as available. 32 day leases are required to avoid the 14.45% Massachusetts Lodging tax.

Contact: Lynda, Property ID: 19124

Spacious cottage near Pleasant Bay with new outdoor sauna
2BR
2 baths
Sleeps 7

We will consider long-term (month +) rentals. However, due to its seasonal nature, we are required to shut our cottage down between November and Marc...

Contact: Gail McCullagh, Property ID: 12283

Charming Restored Cottage: The Summer House in East Orleans
3BR
2 baths
Sleeps 6

Available monthly off season: price ranges from $3,000per month to $5000. Call for more information.

Contact: Jim, Property ID: 28852

Peaceful Contemporary - On Private Wooded Lot
3BR
2 baths
Sleeps 6

Available for long-term winter rental.

Contact: Louis Morongell, Property ID: 32809

Two bedroom home with AC on luminous Crystal Lake
2BR
1 ½ bath
Sleeps 6

November to April. $3000/month; 6 month lease.

Contact: Kamesh, Property ID: 30757

Welcome to our Orleans Escape!
2BR
1 bath
Sleeps 5

Inquire

Contact: Cindy, Property ID: 31244

Mimi's House: 2 Bedroom Home w/a Firepit & Central AC
2BR
1 bath
Sleeps 5

Available

Contact: John, Property ID: 27515

Fish, Swim, Kayak (supplied) in safe, clean pond.
2BR
1 bath
Sleeps 5

Available for long-term winter rental from November to June. $5000 per month

Contact: Louis Morongell, Property ID: 28481

Delightful Cape Cod Cottage! Orleans Charm at it's Finest.
2BR
1 bath
Sleeps 5

Winter rental available December 1st 2021 to May 31st 2022 at a rate of $1,800 / mo + utilities.

Contact: Kara, Property Manager, Cape Peninsula Properties, Property ID: 34864

Cute Cape Cottage
2BR
1 bath
Sleeps 4

We will consider multi-month rentals from Oct 15 thru May 15. Monthly rent will be about $1850-$2,000/month depending on length of time and utilities....

Contact: Beth , Property ID: 28618

Cape Carriage House Getaway!
2BR
1 bath
Sleeps 4

For long-term winter availability, please contact us. $1200-$1500 per month

Contact: Outi and David Baker, Property ID: 20597