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Long-Term Vacation Rentals on Lower Cape Cod

A long-term rental is considered to be an extended stay of more than 31 days. 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). Massachusetts Landlord Tenant Laws will apply.

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

# of Rentals: 53

Brewster

Brewster Dennis town line Rental
Beautiful Home Close to Beaches, Sesuit Harbor & Golf
5BR
4 baths
Sleeps 12

'October to May for $3,400 per month, depending on length of stay. Includes utilities.'

Contact: Gerry or Cindy, ID: 19604

Brewster Rental
Charming Cape - Steps to Greenland Pond!
4BR
2 baths
Sleeps 11

Available for Monthly Rentals in the off season (Oct - April) starting at $3500/month, please inquire for more info.

Contact: Emily LaPierre, ID: 38671

Brewster Rental
Charming 4 Bedroom Home near Breakwater Beach
4BR
2 baths
Sleeps 10

Off season rental at $2300 per month October-May plus utilities.

Contact: John , ID: 23161

Brewster Rental
Cape Retreat+Water Views - Pet Friendly!
3BR
2 baths
Sleeps 10

This property is available in the off season (Nov - April) for monthly stays - starting at $3,000/month and includes utilities.

Contact: Emily LaPierre, ID: 40017

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

Starting early January this property is available for long term rental around 3200 per month!

Contact: Allan and Jenn Peterson, ID: 19423

Brewster Rental
Walk to beach/shops from coveted Paine's Creek neighborhood
4BR
2 baths
Sleeps 8

Inquire about September through May rentals for $4,000/month

Contact: Mike, ID: 31725

At Greenland Pond Rental
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: Merritt Harris, ID: 35643

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

Available from October-May for $1000-2000/month (negotiable). If looking to retire on the Cape or just wintering and you need a wonderful place to sta...

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

Brewster Rental
Charming Cottage, Walk/Cycle to Beach/Shops/Cafes
3BR
1 bath
Sleeps 6

Winter rental $1850/month. Wifi & Utilities included. Minimum 6 month lease. Available Feb-April. No pets. Fabulous location in heart of historic Brew...

Contact: Victoria Majewski, ID: 12130

East Brewster Rental
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, ID: 12150

Chatham

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

Possible. $3500 per month plus utilities

Contact: Harvey Ross, ID: 9648

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

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

Contact: Wendy Gruenberg, ID: 16695

Chatham Rental
Windswept
4BR
2 baths
Sleeps 9

The rental can be rented for 32 nights or longer, if the calendar allows it... Stay longer and save the 14.45% rental tax!

Contact: Pine Acres Rentals, ID: 39991

Chatham Rental
Secluded charming home off of Main Street/Walk to Beach
4BR
2 ½ baths
Sleeps 8

1 month or more $16,000

Contact: Courtney, ID: 39782

Chatham Rental
Spacious Family Home near Ridgevale Beach!
3BR
2 baths
Sleeps 8

Open to longer rentals, if the calendar allows.. Stay 32 nights or longer and save on the 14.45 rental tax!

Contact: Pine Acres Rentals, ID: 39993

Chatham Rental
Views of Bucks Creek!
3BR
3 baths
Sleeps 8

If the calendar allows, the house can be rented for 32 nights or longer, book it and avoid the 14.45% short term rental tax

Contact: Karen at Pine Acres Rentals, ID: 40116

Chatham Rental
Charming Family Cape, Impeccably Landscaped With Ocean Views
3BR
2 baths
Sleeps 8

$4000/mo. We welcome the opportunity to discuss off-season, long term rentals (October - May). Please reach out for more information should you be in...

Contact: Justin, ID: 38971

Chatham Rental
Chatham Beach Chic 5 STAR Family retreat-5 min walk to Beach
3BR
2 baths
Sleeps 8

There is no 14.45% Lodging Tax for stays of 31 nights or more.

Contact: John Muldoon, ID: 24757

Chatham Rental
Private and Peaceful in the Heart of Chatham!
4BR
3 baths
Sleeps 7

Open to longer term rentals, if the calendar allows it.. Stay 32 nights or longer and save the 14.45% rental tax!

Contact: Pine Acres Rentals, ID: 39997

Chatham Rental
Charming Chatham Bungalow-Minutes to Downtown and Beaches
3BR
1 bath
Sleeps 7

We are always looking for off-season or longer term renters as well. Message us for longer term rentals so we can discuss the details. Average monthl...

Contact: Allison Warren, ID: 40064

S. Chatham Rental
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, ID: 25053

Chatham Rental
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, ID: 23722

Chatham Rental
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, ID: 28980

Chatham Rental
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. Small pets considere...

Contact: Catherine Batcheller, ID: 20787

Chatham Rental
Steps to Downtown Chatham and Lighthouse Beach
3BR
2 baths
Sleeps 5

The rental is open to rentals 32 nights or longer, if the calendar allows it. Save the Rental Tax and Stay Longer!

Contact: Pine Acres Rentals, ID: 39987

South Chatham Rental
OOHLAHLAH Charming, Cozy Cottage, Walk to Beach
2BR
2 baths
Sleeps 5

30-day minimum stay May 28-June 28, 2025 = $8000.00 June 28-July 26, 2025 = $10,000.00 July 26-August 30, 2025= $10,000.00 August 30-October 4 = $...

Contact: Allen, ID: 40037

Chatham Rental
Chatham Charmer, Walk-to-Town & Beach!
2BR
1 bath
Sleeps 4

Off season in Chatham? Yes please! This cottage is a perfect fit for a single person or a couple looking to be in Chatham for the winter. $2,300/mo c...

Contact: Sean Pope, ID: 25326

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

The cottage is available for single occupancy only in the off-season Oct. - May as a monthly rental for $1200/mo. All utilities included.

Contact: Carol, ID: 30589

Harwich

Harwich Captain’s Hill Rental
Main House & 2 Efficiencies;Close to Beach & Nantucket Ferry
8BR
5 baths
Sleeps 20

October 1, 2024 to April 15, 2025 $3,500 Main house only - does not include efficiencies

Contact: Andrea, ID: 39195

Harwich Rental
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, ID: 12069

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

October through April; $3,000/month

Contact: Lori, ID: 21491

Harwich Rental
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, ID: 13970

HarwichPort Rental
Spacious Kid-Friendly Home; Walk to Red River Beach
4BR
2 ½ baths
Sleeps 10

Open to longer terms rentals - $7,000-$8000/month

Contact: Bill, ID: 39756

Harwich Port Rental
Harwich Port Beach Home W/Ac, 3/10 Mile To Beach
4BR
2 ½ baths
Sleeps 8

This home will be offered as a one bedroom home at winter season (from Jan -March) from $1300; Nov & Dec & April from $1700/mo plus all utilities for...

Contact: Nina, ID: 31116

Harwich Rental
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, ID: 26783

West Harwich Rental
Classic Cape Vacation - Big Yard & Walking Distance to Lots!
3BR
2 baths
Sleeps 8

October through April; $3,500/month

Contact: Patrick, ID: 22324

Harwich Rental
Renovated Modern Home with Firepit, Outdoor Shower & More
3BR
2 baths
Sleeps 7

Monthly rental available - October through May $3600-$3,800/mo. Please inquire

Contact: Jeff, ID: 39358

Harwich — on Long Pond Rental
Perfect Location: Private Beach & Rail Trail Access
3BR
2 baths
Sleeps 6

Long term or monthly rentals are available at $12,000/month (June-September) or $4,500 (October-May).

Contact: Peter, ID: 39768

Harwichport Rental
Harwicport-Beaches-Restaurants-Ice Cream
3BR
1 bath
Sleeps 6

September through end of April Price range per month is $2500-$3500

Contact: Eric, ID: 39066

Harwich Port Rental
Harwich Port Walk to Everything! Long Term Rental Available
3BR
1 bath
Sleeps 6

Long Term Rental Available by the Month of Season $12k to $24K

Contact: Sean Kearney, ID: 7091

Harwich Port Rental
Two Bedroom with Loft Luxury Home
2BR
1 bath
Sleeps 4

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

Contact: Michael McNally or Chris Sage, ID: 22987

Harwich Rental
Vacation Escape on Cape Cod Bike Trail
2BR
1 ½ bath
Sleeps 4

Long-Term Rentals for off-season only (September-May). $2,300 per month or weekly at $575 (2-week minimum for off-season rentals).

Contact: Victoria Ekstrom High, ID: 38846

Harwich Port Rental
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, ID: 22990

Orleans

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

Rental Fee: Price Range $60,000 - $125,000. Inquire about 2025 Special! Experience Cape at the Luxury Estate. We offer long-term rentals in June, J...

Contact: Alex, ID: 14224

Orleans Rental
Beautiful, 5 BR/5 BA w/Gust Ste. Perfect for 2 Families
5BR
5 baths
Sleeps 11

Rates depend on Month chosen, from $14,500-21,500.00 per month

Contact: Raymond, ID: 32244

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

October to May monthly rentals available. $3000 - $4000/mo.

Contact: Ruth, ID: 20703

East Orleans Rental
Beautiful Nauset Beach 4 Br Home, A/C, Wifi
4BR
3 baths
Sleeps 8

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, ID: 9286

Orleans Rental
Fits 2 Families, 3+ bedroom, Kid & Dog Friendly, Charming
3BR
2 ½ baths
Sleeps 8

Our home is available for long term rental in the shoulder and winter seasons. The price per month ranges from $4000 for one month and can go as low a...

Contact: Carrie, ID: 29389

Orleans Rental
Pleasant Bay with Private Beach Use
3BR
3 baths
Sleeps 6

Long term rental is available for 3 bedroom/3bath home from January 15th - April 15th at $5,000 a month. Proration for less than 30 days.

Contact: Tracy, ID: 35950

East Orleans Rental
Parson's Cottage
3BR
2 baths
Sleeps 6

$2,500 per month, includes all utility charges. Orleans location, opposite Nauset Farm Shop, 3-bed, 2-bath home, fully furnished available Nov 1 - May...

Contact: Richard, ID: 36644

East Orleans, Barley Neck Rd o Rental
East Orleans Old Cape Vacation Cottage
2BR
1 bath
Sleeps 6

Will consider off season rental, please contact us to discuss. $2600-2800 per month during the fall, winter, spring season. Summertime monthly rental ...

Contact: Patty Doshier, ID: 9996

Orleans Rental
Perfect Cape Cottage Close to Nauset Ocean and Village :
2BR
1 bath
Sleeps 4

Months of June, July & September offered for rent long term at a discount of $6000 - $7500

Contact: Dolores, ID: 38839

East Orleans Rental
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 $1950-$2,200/month depending on length of time and utilities....

Contact: Beth , ID: 28618