50 Best Orleans Apartments on Holiday Lettings - Vacation rentals

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244 Vacation rentals

20

Home rental in Orleans

Cape Cod / Orleans

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Our home is located in a quiet upscale neighbourhood close to all amenities. Walk to grocery store, downtown shopping, library, tennis courts and town field. Less than a 5 minute drive to ocean and bay. Quick access to highway and all the surrounding Cape towns. Rel …see more

from $200 / night

$1400 - $1800 / week

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from $200 / night

17

Apartment rental in Orleans

Cape Cod / Orleans

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
2 bedroom 1 bath apartment with separate private entrance, driveway and deck. Living room, kitchen, and laundry. Queen bed in one room and a double bed in the other room. Optional air mattress can be set up in living room to sleep 2 more if needed. Window AC units in b …see more

from $175 / night

$1225 / week

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from $175 / night

46

Vacation home with swimming pool in Orleans

Cape Cod / Orleans

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
Luxurious Orleans Home with Private Salt Pool, Sleeps 10 (linens included) Peak Summer Weekly Rates: $9,000 - $9,500 (Rents Saturday to Saturday during peak season) Located on a large private lot in South Orleans, this luxurious property provides the highest level of am …see more

from $715 / night

$5000 - $9500 / week

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from $715 / night

36

Vacation home in Orleans

Cape Cod / Orleans

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
Elevated ocean views, walk to Nauset Beach. Linens included. Peak Summer Weekly Rates: $4,500 - $5,200 (Rents Saturday to Saturday during peak season) This spacious East Orleans home is located just off Nauset Beach in the desirable Grand View neighborhood. This neighbo …see more

from $715 / night

$5000 - $5300 / week

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from $715 / night

40

Vacation home in Orleans

Cape Cod / Orleans

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Newly remodeled historic home. Heated Pool, Central AC, Sleeps 12, Linens & Towels Included! Peak Summer Weekly Rates: $9,500 (Rents Saturday - Saturday during peak season) This beautiful 1920 Orleans home, newly remodeled and redecorated, exudes Cape Cod charm, retains …see more

from $750 / night

$4000 - $9500 / week

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from $750 / night

19

Vacation home in Orleans

Cape Cod / Orleans

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
New and upscale with guest house, walk to Skaket Beach $3,500 - $3,800 prime summer weekly rate (Rents Saturday - Saturday during peak season) This home is about a 10 minute walk to Skaket Beach or a very short drive. It's less than a mile (0.8 miles) to the bike trail …see more

from $243 / night

$1700 - $3800 / week

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from $243 / night

(1) Very Good 

20

Orleans Vacation home rental

Cape Cod / Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
Breathtaking views of Nauset Harbor and tucked away at the end of a private drive. With cathedral ceilings and lots of windows, this cottage offers spectacular waterviews from almost every room. The sun rises over the dunes and harbor right into both sitting rooms and …see more

from $458 / night

$3200 - $3500 / week

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from $458 / night

23

Vacation home rental

Cape Cod / Orleans

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Secluded Cape Cottage, 3-5 Minute Walk to Beach $2,100 PRIME SUMMER WEEKLY RATE (Rents Saturday - Saturday during peak season) It's possibly one of the best values in Orleans. Located on the Bayside of Orleans, this well-maintained cottage is one of 4 homes on a 25 acre …see more

from $173 / night

$1200 - $2100 / week

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from $173 / night

17

Vacation home in Orleans

Cape Cod / Orleans

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Pet friendly
Salt waterfront home located in the Ocean Harbor Association in East Orleans. This newly-furnished home is set on over an acre of beautiful multi-level grounds with frontage and views of Little Cove. Enjoy kayaking right from your backyard, access to the association ten …see more

from $415 / night

$2900 - $3500 / week

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from $415 / night

32

Home rental in Orleans

Cape Cod / Orleans

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Sweeping Bay Views, Privacy, Two Full Kitchens (Pets Considered) Peak Summer Weekly Rates: $4,300 - $4,500 (Rents Saturday - Saturday during peak season) This unique vacation home is nestled between Rock Harbor to the east and Skaket beach to the west. The home has its …see more

from $286 / night

$2000 - $4500 / week

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from $286 / night

15

Orleans Vacation home rental

Cape Cod / Orleans

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Air conditioning
Charming modern waterfront cottage-- now with A/C!-- located in the exclusive Mayflower Point section of Orleans where the Namequoit River meets Little Pleasant Bay. The secluded area boasts scenic water views, quiet nights and sounds of birds. The living space has a ne …see more

from $158 / night

$1100 - $1350 / week

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from $158 / night

16

Home rental in Orleans

Cape Cod / Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
This lovely Contemporary Cape sits on almost an acre of land only 2/10ths of a mile from the sandy shore of Bakers Pond and 3/10 mile from Nickerson State Park (in Brewster). Light and bright throughout, this custom home features an open floor plan, gleaming hardwood fl …see more

from $229 / night

$1600 - $2000 / week

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from $229 / night

31

Vacation home in Orleans

Cape Cod / Orleans

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Spacious Bay Side Orleans Waterfront Home Next to Skaket Beach PEAK SUMMER WEEKLY RATE: 8,500 (linens included) Situated between Skaket Beach and Rock Harbor, this magnificent home leaves nothing to be desired. Commanding views and direct access to private beach land co …see more

from $750 / night

$4250 - $8500 / week

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from $750 / night

11

Vacation home in Orleans

Cape Cod / Orleans

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
This delightful, newly renovated and furnished cottage is situated on 1.5 acres of land and offers peace and quiet - right on Pilgrim Lake in Orleans! Central A/C has been added for the summer season!!! This two bedroom, one bath cottage is perfect for a couple or small …see more

from $172 / night

$1200 - $1750 / week

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from $172 / night

24

Home rental in Orleans

Cape Cod / Orleans

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
#501 Viking Cottage: New renovation, sunny secluded home with view & access to saltwater. Enjoy the pleasures of a waterfront property -- Wake up to views of a peaceful Pleasant Bay inlet from this sun-filled, modern 3-bedroom cottage in the woods. Launch your kayak or …see more

from $175 / night

$1399 - $2599 / week

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from $175 / night

18

Orleans Vacation home rental

Cape Cod / Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
This custom designed home was renovated just a couple years ago and is newly furnished and tastefully decorated. It has all the comforts and conveniences of home: bedroom A/C units on each floor; GenAir cook top with grill and griddle; double oven; gas & charcoal grills …see more

from $208 / night

$1450 - $1850 / week

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from $208 / night

16

Vacation home with swimming pool in Orleans

Cape Cod / Orleans

4 15 Min stay varies

  • 4 bedrooms
  • Sleeps 15
  • Min stay varies
  • Swimming pool
  • Child friendly
Private Orleans resort with water views, heated pool & spa; sleeps 14 (linens included) NEW Listing for 2017! (more photos to come when renovations are complete, these photos are from the previous owner) Peak Summer Weekly Rates: $15,900- $16,900 JUST REDUCED -- weeks o …see more

from $1559 / night

$10900 - $16900 / week

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from $1559 / night

15

Home rental in Orleans

Cape Cod / Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Chill out (now with central A/C!) and relax at this wonderful waterfront retreat located in Mayflower Point. This charming cottage offers wonderful views of Lonnie's Pond and Kent's Point and has its own path to Lonnie's River leading out to Pleasant Bay. Perfect for bo …see more

from $143 / night

$1000 - $2250 / week

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from $143 / night

20

Orleans Vacation home rental

Cape Cod / Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Brand new renovation! Light and bright expansive ranch that has been beautifully and thoughtfully upgraded throughout. This architech-designed 'green' home is pristine and feels brand new! A few of its many highlights are its wonderful great room offering additional liv …see more

from $358 / night

$2500 - $2900 / week

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from $358 / night

(1) Excellent 

31

Orleans Vacation home rental

Cape Cod / Orleans

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Located on the bank of Rock Harbor Creek, this 5 BR, 4 Bath classic Cape has all you and your family are looking for this summer. The large second floor master suite overlooks the marsh with an attached private bedroom with 2 twins where the little ones can dream away, …see more

from $386 / night

$2700 - $3000 / week

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from $386 / night

12

Vacation home in Orleans

Cape Cod / Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
True Cape Cod Charm in every way! This 3 bedroom Saltbox is just up the road from Nauset Beach. All the upgraded conveniences you could want including granite counters, hardwood floors, washer/dryer, WIFI and air conditioning. Relax in the outdoor shower or cook on …see more

from $143 / night

$1000 - $2000 / week

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from $143 / night

21

Vacation home in Orleans

Cape Cod / Orleans

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning
Designed to look like an illustration from a children’s fairytale, this gracious and comfortable vacation home promises a magical vacation any time of the year. Enter through lush gardens into a surprisingly spacious, fully air conditioned home designed with relaxation, …see more

from $286 / night

$2000 - $3500 / week

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from $286 / night

24

Vacation home in Orleans

Cape Cod / Orleans

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
Walk to the water from this private 4 bedroom, three bath home. Just one house away from a waterview and 200 yards to deeded access to a cove off The River. Nestled within two acres on a gorgeous country dead end road. The sandy beach of Crystal Lake is only .4 mile w …see more

from $231 / night

$2500 - $3000 / week

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from $231 / night

13

Vacation home in Orleans

Cape Cod / Orleans

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
Beautiful 4 bedroom home on private cul de sac in East Orleans. Pristine landscaped yard with swing set and hammock. Big kitchen that opens to the family room. Open den with tv and couches. Full bath, washer & dryer on the first floor. Upstairs has 3 large bedrooms with …see more

from $358 / night

$2500 - $3800 / week

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from $358 / night

18

Orleans Vacation home rental

Cape Cod / Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
At the end of a private lane lies your secluded vacation retreat on tranquil Pilgrim Lake. Just 60 feet from the decks and living room window is your private lakefront with boat dock for swimming, boating or fishing. The main deck, overlooking the water with comfortable …see more

from $272 / night

$1900 - $2900 / week

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from $272 / night

16

Vacation home in Orleans

Cape Cod / Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
Overlooking the salt waters of Mill Pond and located in grand Ocean Harbor Estates! The Atlantic Ocean is just beyond this amazing waterway. Only 2 miles from Nauset Beach and 1.5 miles to East Orleans Village. This property has it all. Views, association dock and tenn …see more

from $686 / night

$4800 / week

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from $686 / night

(1) Excellent 

19

Home rental in Orleans

Cape Cod / Orleans

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
*If you can't find the dates available that you are looking for, we also have a second studio you may be interested in. Send us an inquiry and we will try to help you find the dates you want.* Beach Rose is a studio in “Holly Tree Cottages” available by world-renowned …see more

from $89 / night

$600 - $1199 / week

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from $89 / night

19

Home rental in Orleans

Cape Cod / Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
This 3 Bedroom 2.5 bath retreat with Central AC is hidden away down a semi private drive in East Orleans. It has large sliding glass doors down one side of the home off the living room offering lots of light. Mid century modern decor fills this clean lined living space. …see more

from $122 / night

$850 - $3450 / week

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from $122 / night

16

Vacation home in Orleans

Cape Cod / Orleans

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Price Range $2000-$3500 NEW LISTING! PROPERTY UNDERGOING COSMETIC UPGRADES! NEW PICTURES COMING SOON! The moment you arrive at this 3 bedroom, 3 bath classic cape with central a/c, you will immediately downshift into vacation gear. Sited on a knoll in East Orleans, the …see more

from $286 / night

$2000 - $3500 / week

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from $286 / night

27

Orleans Vacation home rental

Cape Cod / Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Pet friendly
This beautiful Cape Cod home sits on Barley Neck, which is small peninsula just a few minutes drive to Nauset Beach. It is surrounded by Meeting House Pond and Little Pleasant Bay. This area is harbored from the Atlantic Ocean by Pochet Island. From this location, you …see more

from $129 / night

$900 - $3550 / week

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from $129 / night

(1) Excellent 

15

Vacation home in Orleans

Cape Cod / Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Rare opportunity to vacation in Nauset Heights right on the waterfront! Perfect Beach House for the beach loving family or couple. Walk out the door to one of Cape Cods most beautiful beaches. Swim, fish, sunbath or take gorgeous walks for miles along the National Seas …see more

from $468 / night

$3275 - $4750 / week

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from $468 / night

22

Vacation home with swimming pool in Orleans

Cape Cod / Orleans

4 14 7 nights min

  • 4 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This exceptional compound is one-of-a-kind with a Main House, Carriage House and private pool. The Main house has a restaurant quality kitchen which will bring out the Iron Chef in you. Ample seating in the dining area with separate bar. Entertaining is easy in the L …see more

from $643 / night

$4500 - $10000 / week

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from $643 / night

19

Vacation home in Orleans

Cape Cod / Orleans

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Renovated Gem on Town Cove in Orleans with hot tub, walk to town Peak Summer Weeks: $4,400 - $5,400 Please note:  This property rents Sunday to Sunday in summer for full-week or multiple week terms only, but is available during the shoulder-season for 3-night minimum. T …see more

from $429 / night

$2500 - $3200 / week

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from $429 / night

(1) Excellent 

15

Home rental in Orleans

Cape Cod / Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
This private gem sits at the end of a sandy lane wrapped in trees and bathed in sunlight. The front deck welcomes you to sit and relax and enjoy the peace and quiet and plan your next days adventure. Located less the 2 miles from Nauset Beach and slightly farther from …see more

from $172 / night

$1200 - $2000 / week

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from $172 / night

16

Vacation home rental

Cape Cod / Orleans

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
WATERFRONT on Bakers Pond! Take the path from the patio to your private pondfront to enjoy swimming, fishing and kayaking on this lovely freshwater pond. Designed as an airy contemporary cabin on 3 levels-- all with sunset water views-- this home has beautiful pine pane …see more

from $286 / night

$2000 - $2200 / week

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from $286 / night

11

Vacation home rental

Cape Cod / Orleans

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Child friendly
Adorable cottage located in a beautiful, quiet area about 3/10ths of a mile from Nauset Harbor. The cozy living/dining/kitchen area features a brand new kitchen, queen sofa bed and A/C unit. The bedroom has a king bed (easily converted into 2 twins) and an A/C unit. A s …see more

from $108 / night

$750 - $1100 / week

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from $108 / night

30

Vacation home in Orleans

Cape Cod / Orleans

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
2013 WATERFRONT HOME! Gorgeous 3-level contemporary home with 180 degree view of a beautiful 28-acre lake and conservation lands. With water views from every room, this dramatic home has 3 exterior decks and a private path to the pond only 75 feet away. Set on a cul-de- …see more

from $572 / night

$4000 - $4200 / week

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from $572 / night

26

Vacation home in Orleans

Cape Cod / Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
Light and bright spacious beach house sitting on the edge of a marsh at the end of a sandy lane-- just 2/10ths of a mile from Skaket Beach! This wonderful spot offers panoramic marsh views with peeks out to the waters of Cape Cod Bay. The recently renovated main floor c …see more

from $315 / night

$2200 - $2900 / week

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from $315 / night

16

Home rental in Orleans

Cape Cod / Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Charming remodeled 1930s cottage! This home is located in the desirable and scenic Mill Pond area in Orleans with a well kept yard and wrap-around deck. House is very comfortable with single story living. Three bedrooms (brand new mattresses) and 1 and a half baths …see more

from $143 / night

$1000 - $1300 / week

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from $143 / night

20

Vacation home in Orleans

Cape Cod / Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Newly renovated ranch located on a cul-de-sac in the desirable Brick Hill area of East Orleans. Fresh, bright and open with Central Air Conditioning! Enjoy the newer furnishings throughout and all amenities. A great spot convenient to the sandy shore of Nauset Beach and …see more

from $300 / night

$2100 / week

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from $300 / night

1