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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: 40

Brewster

Brewster Rental
Renovated Brewster Beach House + Cottage Near Bay Beaches
4BR
3 baths
Sleeps 12

Case-by-case basis. Monthly rentals begin at $3500 and vary by month. Please inquire for details.

Contact: Christine Fiske, ID: 33519

At Greenland Pond Rental
Renovated Coastal Farmhouse at Greenland Pond
3BR
2 baths
Sleeps 9

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

Contact: Christine Fiske, ID: 35643

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

Starting early January 2026, this property is available for long term rental around 3200 per month!

Contact: Allan and Jenn Peterson, ID: 19423

Brewster Rental
Single Level, Sun Filled, Family Retreat - 4 Seasons
3BR
2 baths
Sleeps 8

Long term rental available September - May. 4 month min. $3000-$4000 a month plus utilities.

Contact: Elizabeth, ID: 33496

Brewster Rental
Private Retreat on 2 Acres; Walk/Bike to 3 Brewster Beaches
3BR
2 baths
Sleeps 8

Available Sept - Dec 2026 $3,000-4,000/mo negotiable

Contact: Kathy, ID: 40197

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

Winter rental $1800/month. Minimum 5 month lease. No pets. Fabulous location in heart of historic Brewster! Must have great references.

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

Brewster Rental
Charming Historic Home, Walk to the Beach
3BR
1 bath
Sleeps 5

Available for long term rental September - May. $3000-$4000 per month.

Contact: Elizabeth, ID: 41823

West Brewster Rental
Cranberry Cottage: Cozy, Convenient, Charming, and Cool!
2BR
1 bath
Sleeps 4

Contact owner for long-term rental. Monthly rate ranges from $2,000-$10,000 depending on season.

Contact: Christy Johnson, ID: 41031

Chatham

Chatham Rental
Coveted Chatham Location
5BR
2 ½ baths
Sleeps 10

if the calendar allows it.

Contact: Pine Acres Rentals, ID: 41716

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

1 month or more starting at $14,000

Contact: Courtney, ID: 39782

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. Average monthly price is approximately $3000-$3,200 a month depending on length...

Contact: Allison Warren, ID: 40064

Chatham Oceanfront Condos Rental
RENOVATED KITCHEN! Beachfront Condo Walkable to Downtown.
2BR
1 ½ bath
Sleeps 7

Long-term rentals welcome. Weekly rental rates range from $6,000 to $9,200 per mo. Save when you book for a month and save more when you book before J...

Contact: Lynnette, ID: 39812

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

Available approx November through May. $1400-$3500 monthly depending upon length of stay, plus utilities. Small pets considered ($40). Non refundable ...

Contact: Catherine Batcheller, ID: 20787

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
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
Sleep under the stars, walk to Hardings Beach - dog friendly
3BR
1 ½ bath
Sleeps 6

$10,400/mo for long term high season rental.

Contact: Susan , ID: 31299

Chatham Rental
Oceanside Townhouse Steps to Private Beach
2BR
1 bath
Sleeps 4

2 weeks up to 4 months during off season $2500 plus $85 internet plus monthly electric bill

Contact: David Brady, ID: 37222

Chatham Rental
Cozy Oceanfront Townhouse; Steps to Private Beach
2BR
1 bath
Sleeps 4

Off season November first to May first 2 weeks to Monthly $2500 per month + $85 + electric bill during stay.

Contact: Dave, ID: 39699

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

Off season in Chatham? Yes please! $2,350/mo covers all utilities except snow removal. Walk to everything in Chatham, the Cape Cod RTA bus stops at th...

Contact: Sean Pope, ID: 25326

Harwich

HarwichPort Rental
Spacious Kid-Friendly Home; Walk to Red River Beach - 5star!
4BR
2 ½ baths
Sleeps 10

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

Contact: Bill, ID: 39756

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

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

Harwich Rental
Cape Breeze – Renovated 3BR + Den, Big Yard & Outdoor Shower
3BR
2 baths
Sleeps 8

Open to monthly, yearly rental. 5% discount for 4 weeks in season $5-8k/mo off season rental (Oct 15-May 15)

Contact: Shannon, ID: 40383

Harwichport Rental
Well appointed, Private Yard, Super Clean, AC, Walk to Beach
3BR
2 ½ baths
Sleeps 8

Off Season rental available. $2400 per month plus utilities. History of excellent winter rentals. Utility history available.

Contact: Karen, ID: 33503

Harwichport Rental
Walk to beach- Sweet, Clean Cottage w King Bed & Central AC
3BR
1 ½ bath
Sleeps 7

Available for off season rental. $2000 per month plus utilities.

Contact: Karen, ID: 34043

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

Open for Winter season 10/1/26- 5/22/27 rental at $2200 / month plus utilities.

Contact: Laura and Jim, ID: 29274

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

Monthly rental available - October 2025 through May 2026. $3600-$3,800/mo. Please inquire

Contact: Jeff, ID: 39358

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

West Harwich Rental
Ocean Views & Private Beach, Saltwater Pool, Tennis, Bocce
2BR
2 baths
Sleeps 6

Monthly rental June-October 2026. $11,500-15,000/mo

Contact: Alexandra, ID: 40842

East Harwich Rental
Beautiful Pond Front Contemporary Home / Quiet and Private
2BR
2 baths
Sleeps 6

Available October 1st through May 31st as a 6–8 month off-season rental for $1,950/month. Please reach out for more details.

Contact: Jeff or Phil, ID: 40195

Harwich Rental
Get Swept Away - Cozy Cottage across from Nantucket Sound
2BR
1 ½ bath
Sleeps 6

Summer long term rental available for the months of June, July and August 2026. $12,000/mo.

Contact: Ellen Collins, ID: 40317

Harwichport Rental
Near Bank St & Sea St. Beaches!
4BR
1 ½ bath
Sleeps 5

June 18-July 18 $12,300.00 includes cleaning, No added fees! Stay 31 days includes July 4th holiday. Perfect for a family of 5 or less!

Contact: Susan Palermo, ID: 23970

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

This Luxury home is available for winter rental at $2000 per month . Minimum winter rental is 6 months minimum.

Contact: Chris Sage, ID: 22987

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

Long-term rentals for $2,000 per month in the off-season, or $6,600 per month on season.

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: Chris Sage, ID: 22990

Harwich Port Rental
Great location In Town Harwich Port
1BR
1 bath
Sleeps 2

Available from November first to May first. $1300 per month + $60 internet fee + electric bill every month.

Contact: David Brady, ID: 33804

Orleans

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