Long-Term Vacation Rentals in Dennis

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).

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

Filter By Area or Town

Cape Cod

Upper Cape Cod

Mid Cape Cod

Lower Cape Cod

Outer Cape Cod

Just Off Cape

Martha's Vineyard

Nantucket

# of Rentals: 22

Dennis

Main House and Adjoining Cottage - Great for Large Families

6BR

3 ½ baths

Sleeps 15

Available for Long-term winter rentals - Cottage is NOT included since it is not winterized Price range from $3,400 to 4,000

Contact: Kim, Property ID: 18302

Beautiful Quiet Private East Dennis Home for Rent Sleeps 12

5BR

3 ½ baths

Sleeps 12

Available for monthly rentals from mid-september until thanksgiving week. And from mid-february until mid-may. Price range from $9000 to $12000

Contact: Jonathan , Property ID: 11848

Now renting through HomeLand Realty in Dennis 508-385-1331

5BR

2 ½ baths

Sleeps 12

Winter rentals are considered. Price $3,500 per month including utilities. Please contact for further information. Thank you!

Contact: Allen & Tania, Property ID: 26759

Walk to Corporation Beach; A/C; Close to Golf, Shops, Dining

4BR

2 baths

Sleeps 12

Long term rental is available for off-season. September 2024 thru June 2025. Price range ($2,300 monthly; long term rate available)

Contact: Moe, Property ID: 39497

Quivet Neck Beauty - Walk to Sea Street/Cold Storage Beach

4BR

3 baths

Sleeps 10

$3500/month in off season, from roughly October-April

Contact: Billy Hartmann, Property ID: 38985

Central Air/New kitchen/baths 4Bed/2.5Ba North of 6A

4BR

2 ½ baths

Sleeps 10

October through April or May. $3200-$6000/mo

Contact: Caitlin, Property ID: 29759

Walk to Beach Cape House with 4 Bedrooms/2 Baths and AC

4BR

2 baths

Sleeps 8

Long-term winter rentals available upon request. Please reach out for more information as pricing ranges from $2300 to $2500 per month in December, Ja...

Contact: Laura , Property ID: 32390

Available for Off-Season Sept 18 - June 2025

4BR

2 ½ baths

Sleeps 8

Available 9/15/24: $2250/mo, including internet. The tenant is responsible for gas and electricity. I prefer a total 8-month winter renter, but there ...

Contact: Marsha A., Property ID: 23933

Swan River Retreat - 5 minute walk to the beach!

4BR

2 baths

Sleeps 8

Off-season winter rental available. $2500/mo plus utilities.

Contact: Geri, Property ID: 34493

Olivia Walker Way Cape Escape

3BR

2 baths

Sleeps 8

Available to rent for January, February, and March $2500 a month excluding utilities, Additional $2500 security deposit required

Contact: Michelle, Property ID: 35527

Mayflower Beach and Dennis Village

3BR

2 baths

Sleeps 8

Prices start at $3,800 per month. Winter rentals between late fall and early spring are available under a 1 or 2 bedroom modified floor plan configura...

Contact: James, Property ID: 29177

18th Century Cape Cod House w/its own Beach on Scargo Lake

3BR

2 baths

Sleeps 8

$2,500 a month

Contact: Verity Bostick, Property ID: 9530

100 yards from Bayview Beaches on the North Side

3BR

2 baths

Sleeps 8

Sleeps 6 in 3 BR, 10/1 - 5/15, $2,000. per month plus utilities. Close to beach, golf and shopping. Great getaway house. 1 month security required.

Contact: Tony, Property ID: 10266

2 miles from Mayflower Beach - Olivia’s Cottage

3BR

2 baths

Sleeps 8

Fully Furnished. Utilities Included. Available November to April. $5000 per month

Contact: Robin, Property ID: 38663

Bright & Updated Cottage

3BR

1 bath

Sleeps 7

Available Sept - May $3000/mo, contact for long term inquires and pricing

Contact: SusanneF, Property ID: 36496

Secluded Family/Pet Friendly Home in E. Dennis, Near Beaches

3BR

2 baths

Sleeps 7

Available October through April as a monthly rental. $4,900 per month, includes all heat and utilities (electric, gas, internet, water).

Contact: Ron, Property ID: 37939

Charming Updated Home w/ Central A/C in Heart of Dennisport

3BR

1 bath

Sleeps 6

Available off-season 2024-2025, $1,900 per month, including utilities (gas/electric) with monthly availability Now through mid-June 2025 with a Securi...

Contact: Rich, Property ID: 38206

A Cape Cod Retreat on Scargo Hill - Friday to Friday rental

3BR

2 ½ baths

Sleeps 6

This fully furnished house is available for long term off season rental. It is available October 15 - April 30th for 6000.00 monthly.Housekeeping serv...

Contact: Margaret & Fred Christen, Property ID: 5011

3 Bedroom Ranch - Dennisport - Newly Renovated

3BR

1 bath

Sleeps 6

October through May - $1,750 a month - Utilities Included

Contact: Julie, Property ID: 28120

3BR Ranch. Close to Popular Dennis Beaches with Central Air!

3BR

1 bath

Sleeps 6

$1900 plus utilities September-May or June