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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). 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: 25

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 $3,000 to 3,500

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

Great Home and Location for 2 Families(Sleeps 12)
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

Amazing Ocean Views, 2 Master Suites, Completely Renovated
3BR
3 ½ baths
Sleeps 12

Available November-April at monthly rates. Please inquire for specific rates as they vary by month and length of stay.

Contact: Michelle Kelly, Property ID: 25722

Gorgeous Beachfront Home on the Bay. Two decks, A/C!
5BR
2 ½ baths
Sleeps 10

Long term winter rental available Discounted monthly rates

Contact: Cathy, Property ID: 32893

Renovated Spacious Beach Family Getaway/Walk to Beach
5BR
2 ½ baths
Sleeps 10

This property is available for Long-Term Rental.

Contact: Raymond, Property ID: 36383

Luxury Colonial with Central A/C - Walk to Mayflower Beach
4BR
2 ½ baths
Sleeps 10

...

Contact: Len Holt, Property ID: 29879

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

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

Cozy Cape Cod Family Getaway ~ A/C ~ Screened Porch
3BR
2 baths
Sleeps 8

The house is available for winter rentals. Contact the owner for any inquiries.

Contact: Kat, Property ID: 36198

New listing-Bright, sunny home 1.5 miles to Mayflower Beach
3BR
1 ½ bath
Sleeps 8

House can be used for monthly and year round rental. Price is negotiable. Please contact for details.

Contact: Tracy Coughlan, Property ID: 24103

New home, private, central location, AC, outdoor shower.
3BR
2 baths
Sleeps 8

Johnny A Kelley Recreation area is .5 mile from house with playground, tennis and basketball courts. Cape Cod Rail Trail ( Old Bass River Rd) is 1.1 ...

Contact: Laura , Property ID: 34266

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

East Dennis Bayside Gem - All 5 star reviews!
3BR
2 baths
Sleeps 7

Please inquire if you are interested in a long-term rental

Contact: Mariellen , Property ID: 22675

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

Cape Cod Waterfront Gem w/AC, Boating from Back Yard to Sea
3BR
3 baths
Sleeps 6

This house will be offered as 1 or 2 bedroom winter home from Nov - April for discount rate. Open 1 to 2 bedrooms for up to 2 occupancy. Rate from ...

Contact: Nina, Property ID: 33495

3BR Ranch. Close to Popular Dennis Beaches!
3BR
1 bath
Sleeps 6

$1900 plus utilities September-May or June

Contact: Sheila , Property ID: 32694

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

Captain William House -Newly Renovated
2BR
2 ½ baths
Sleeps 6

Yes October to May

Contact: Karen, Property ID: 34137

18th Century Cape Cod Cottage with Beach on Scargo Lake
2BR
1 bath
Sleeps 6

$1,200 a month until April 30. Utilities are extra.

Contact: Verity Bostick, Property ID: 19306

Sandcastle by the Sea
2BR
1 ½ bath
Sleeps 6

Long term rentals for October, November, December Weekly $3,750.00

Contact: John, Property ID: 36007

Updated, Family-Friendly Getaway -- Close to Everything
2BR
1 bath
Sleeps 6

Long-term, off-season rentals are available in October - March. Please contact for off-season rates.

Contact: Niki, Property ID: 34793

Ocean Front Condo on the beach
2BR
2 baths
Sleeps 5

yes

Contact: Raj, Property ID: 21533

Sunshine On the Water
2BR
1 bath
Sleeps 4

No longer accepting applications for off-season/winter. Thank you to all who inquired!

Contact: Tony & Sarahbeth, Property ID: 25944