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Long-Term Vacation Rentals in Wellfleet

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: 28

Wellfleet

Gorgeous newly renovated house, steps to downtown Wellfleet
5BR
3 ½ baths
Sleeps 10

Also available upon request and rates vary from 1,500 to 2,000 per month.

Contact: Fernanda, Property ID: 20707

Contemporary with Open Floor Plan 2 Blocks from Mayo Beach
5BR
3 ½ baths
Sleeps 10

CALL FOR MONTHLY RATES.

Contact: Eve Lorenz, Property ID: 27256

Impeccable, Newly Renovated 4BR Bayside Cottage
4BR
2 baths
Sleeps 10

If you are looking for a long term winter rental please call Sarah directly at 617-230-1413 to discuss pricing and availability.

Contact: Sarah, Property ID: 8717

Wellfleet Spacious Contemporary, Walk to Town & Bay Beaches
4BR
2 ½ baths
Sleeps 10

This home is available for a long-term winter rental November through March/April. Price negotiable.

Contact: Jessie , Property ID: 13026

Modern 3Br, Hot Tub, Game Room, a/c, Dog Ok, Near Beaches
3BR
2 baths
Sleeps 10

We love winter guests November through March, with monthly price based on occupancy. The house is heated and until recently occupied year round. The s...

Contact: Matt & Marie, Property ID: 31917

Spectacular home on Gull Pond. Short walk to beach
5BR
3 baths
Sleeps 8

Available upon request

Contact: Anne, Property ID: 33825

Chequessett Bluff Road, 4 BR w/AC, 200 yards to Mayo Beach
4BR
2 baths
Sleeps 8

.8 of a mile (3 minute drive) to Chequessett Yacht & Country Club for golf, tennis and sailing. .5 mile to public tennis courts, basketball court and ...

Contact: Richard, Property ID: 32933

Create memories here! Private, close to everything, TREES!
4BR
2 baths
Sleeps 8

No long term winter rental.

Contact: Rebecca Hansen, Property ID: 25891

Stunning Water Views from ''Windward'' on the Bay
4BR
2 ½ baths
Sleeps 8

Windward has been rented by artists and writers for up to 6 months. The fee is much dependent on number of people at the house and how the house is pl...

Contact: Windward, Property ID: 3600

Waterfront.Walls of glass.Views surround.Walk to town.A/C
4BR
2 baths
Sleeps 8

Considered upon request.$6,000-$8,000. Non-refundable deposit required to secure rental, fully refundable damage deposit also required.

Contact: Kathy, Property ID: 5527

Winterwood - Walk to Dyer Pond and village
4BR
2 ½ baths
Sleeps 8

Monthly rates available - October 2022 is $6,000. Will consider 2022-2023 monthly off-season rentals. Please inquire.

Contact: Heidi Ganss Harris, Property ID: 23931

Paine Hollow Pleasure: Water Views & Walk to Beach
4BR
2 baths
Sleeps 8

The house is fully winterized and has a wood burning stove in the living room. Off-season and long-term rentals are possible. $3500 - $2000 month. p...

Contact: Alison Landes, Property ID: 24751

Highland House-Pleasant Point: Peaceful Home w/Central AC
3BR
2 baths
Sleeps 8

The house is available off season. Monthly rate for offseason is $3000/month.

Contact: Ricki, Property ID: 31578

Secluded Gem in Village: 2023 Calendar now posted
3BR
2 baths
Sleeps 8

Monthly rental is available from Oct - May; see rates on the Pricing Calendar. Utilities are included except for trash collection (which is available ...

Contact: Bob and Fran, Property ID: 8592

Charming Seaside Cottage in National Seashore
3BR
1 ½ bath
Sleeps 8

April and May, and also September and October are available for full time rental, at $1000/wk, 3000/mo

Contact: Pamela Blau, Property ID: 9299

3 BR Cottage Near National Seashore and Rail Trail
3BR
3 baths
Sleeps 8

Nov-April, $3,500/month utilities included (FYI - Rentals over 31 days are exempt from the 14.45% short-term rental tax)

Contact: Bill & Joy O'Connor, Property ID: 32564

Special Modern Home
2BR
2 ½ baths
Sleeps 8

Long-terms rentals welcome November-March; $3600 per month including garbage and recycling, cable, wifi, heat and electricity.

Contact: Susan and Clint, Property ID: 25150

Beachside Home at LeCount Hollow Beach with A/C
3BR
2 baths
Sleeps 7

Two excellent golf courses nearby (Chequessett in Wellfleet and Highland in Truro).

Contact: Brian Regan, Property ID: 21479

Hilltop Mid-Century Artist's Home+Separate Studio & View
2BR
1 bath
Sleeps 7

32 day and over rentals in the off-season are negotiable. Rates between $2500 and $5000 per month depending on timing and number of months.

Contact: Jenny, Property ID: 8905

Wellfleet Gem – Close to Beaches and Town, Central A/C
3BR
2 baths
Sleeps 6

September and October monthly rentals available for $6000. Please contact for more details.

Contact: Sheldon, Property ID: 29425

Spacious & Bright with a Screened Porch
3BR
2 baths
Sleeps 6

Off-Season - Monthly and Short term rentals are available.

Contact: Ted or Vanessa, Property ID: 34173

Stylish Cottage in Wellfleet
2BR
1 bath
Sleeps 4

Long-term rental available, tax-free after 30 days. Please email me with your dates and we can discuss off-season rates ($3000-$4000/mo between Novemb...

Contact: Maura, Property ID: 34666

Great Location! 5 Min Walk to Bay Beaches
2BR
1 bath
Sleeps 4

Winter Rental possible from Mid-October to May. 2500 a month with internet included. Other utilities are not included.

Contact: Tim , Property ID: 36530

2 BR Brick Cottage w heat & AC Steps from Mayo Beach
2BR
1 bath
Sleeps 4

This property is perfect for the academic or the artist in need of a peaceful, warm and cozy, getaway to complete academic work or artistic endeavors....

Contact: Rosemary, Property ID: 31649

2 BR Brick Bungalow - 35 Steps from Mayo Beach
2BR
1 bath
Sleeps 4

This property is perfect for the academic or the artist in need of a peaceful, warm and cozy getaway to complete academic work or artistic endeavors. ...

Contact: Rosemary, Property ID: 31695

The Road House at Hidden Hollow
1BR
1 bath
Sleeps 4

Nov-April, $2,400/month utilities included (FYI - Rentals over 31 days are exempt from the 14.45% short-term rental tax)

Contact: Bill & Joy O'Connor, Property ID: 33217

Charming Cottage Overlooking Wellfleet Harbor
2BR
1 bath
Sleeps 2

Sleeps 2 in 2 bedrooms. Discount is available for rentals longer than 1 month. $1,400 - 2,250 per week dependent upon season.

Contact: Joanne, Property ID: 17736

Wellfleet by the Bay
1BR
2 baths
Sleeps 2

Available for multiple month rentals For lower pricing (flexible dates)

Contact: Jay, Property ID: 10650