25 Best Vacation Rentals in South Orleans - Holiday Lettings - Cabins

Close

View larger map

South Orleans

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

27 Vacation rentals

11

Vacation home in South Orleans

Cape Cod / South Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Enjoy this cozy 3 bedroom Cape Cod Cottage in Nauset Village cottage colony! Each bedroom has a full sized bed and the living room provides TV, a DVD player, and plenty of seating for the whole family! The fantastic deck area leads right to the enclosed outdoor shower, …see more

from $129 / night

$900 - $1175 / week

Inquire View

from $129 / night

37

South Orleans Vacation home rental

Cape Cod / South Orleans

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Air conditioning
Central Air and All Amenities! Enjoy Brand New Cape Style Vacation Rental Home in Orleans! Peak Summer Weekly Rates:  last week of June until the first week in September: $5,000/week. The actual Address is 5 White Cedar but for Google Mapping we are using the lot next d …see more

from $572 / night

$4000 - $5000 / week

Inquire View

from $572 / night

26

Home rental in South Orleans

Cape Cod / South Orleans

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Savor soothing views of Pleasant Bay, Nauset Bar and the Ocean beyond! Gorgeous sun and moon rises too! Swim, fish, shell or relax from private beach and dock - 3 minutes - door to dock. A large, sunny & beautifully maintained home in lovely East Egg affords the space a …see more

from $858 / night

$6000 - $6801 / week

Inquire View

from $858 / night

21

Vacation home in South Orleans

Cape Cod / South Orleans

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
6 S. Little Bay Road, South Orleans (ID# 55120) 2017 Season! Lovely home in East Egg Community of South Orleans with views, beach access, central air conditioning and a beautiful expansive yard. Views of Pleasant Bay from almost every room as well as a great brick patio …see more

from $858 / night

$6000 - $6801 / week

Inquire View

from $858 / night

28

South Orleans Vacation home rental

Cape Cod / South Orleans

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Exquisite Custom Built 5BR Home in Orleans, Tons of Stuff for the Kids! Peak Summer Weekly Rates: $6,900-$7,200 If you're looking for upscale accommodations yet plenty for the kids to do, this stunning new home is the one for you. Situated on a quiet cul-de-sac near Ple …see more

from $743 / night

$5200 - $6900 / week

Inquire View

from $743 / night

12

South Orleans Vacation home rental

Cape Cod / South Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Situated in peaceful serenity on a small South Orleans pond, this well-appointed home offers gracious vacation living, privacy and easy access to Nauset and Skaket Beaches, as well as to Orleans and Chatham activities. With 4 bedrooms and 2.5 baths, it sleeps up to 8 ve …see more

from $372 / night

$2600 - $2850 / week

Inquire View

from $372 / night

28

Vacation home in South Orleans

Cape Cod / South Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Enjoy this beautiful South Orleans home with its own private beach. The interior of the home boasts an open floor plan including a kitchen with granite countertops and center island, spacious dining area, livingroom and a first floor Master Suite with a queen and twin s …see more

from $372 / night

$2600 - $5000 / week

Inquire View

from $372 / night

19

South Orleans Vacation home rental

Cape Cod / South Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This very special 3 bedroom, 2 bath home overlooks the Namequoit River and features lovely waterviews, two waterside decks, newly remodeled kitchen and great amenities. The property is very close to Pah Wah Conservation area with hiking trails and a sandy Pleasant Bay b …see more

from $286 / night

$2000 / week

Inquire View

from $286 / night

16

Home rental in South Orleans

Cape Cod / South Orleans

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
This beautiful 4 bedroom, 3 bath South Orleans home is located in a quiet neighborhood, just a short drive to Pleasant Bay. The first level of the home features a spacious kitchen and dining area, large living area with a/c unit, and a Master Suite with a king sized bed …see more

from $258 / night

$1800 - $2400 / week

Inquire View

from $258 / night

20

South Orleans Vacation home rental

Cape Cod / South Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Enjoy all the comforts of home at this 4 bedroom, 2.5 bath pet friendly home! The first level of the home features a living room, kitchen with dining table and full bathroom as well as two bedrooms, one with two twins and one with a queen sized bed. Each bedroom has an …see more

from $158 / night

$1100 - $1701 / week

Inquire View

from $158 / night

33

Vacation home in South Orleans

Cape Cod / South Orleans

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
This beautiful South Orleans home features three levels of living - all with beautiful views of Pleasant Bay and the ocean beyond! Enjoy the shared, private dock and sandy beach just a short walk from the front door of this lovely, contemporary home. The property featur …see more

from $986 / night

$6900 / week

Inquire View

from $986 / night

(1) Excellent 

36

Vacation home in South Orleans

Cape Cod / South Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
This spacious and comfortable 2-story home sits on a wooded lot within a short distance to a boat ramp and just minutes away from Nauset, Skaket and Pleasant Bay beaches. With four bedrooms and 2.5 baths, it sleeps up to 8 comfortably. The first level features a living …see more

from $236 / night

$1650 - $2150 / week

Inquire View

from $236 / night

(2) Very Good 

19

Vacation home in South Orleans

Cape Cod / South Orleans

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
52 Forest Way, Orleans MA (ID# 18423) 2017 Season! Contemporary home with lots of space, nestled in a quiet wooded area of Orleans. This home is ideal for a casual vacation. 5 Bedrooms (2 Queens, 1 Double, 4 Twins) and 3 Baths. No Pets Accepted. Weekly Rental (7 Night M …see more

from $200 / night

$1400 - $1600 / week

Inquire View

from $200 / night

(1) Excellent 

10

Vacation boathouse in South Orleans

Cape Cod / South Orleans

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Private garden
The BoatHouse is unique. Built and furnished in Cape Cod Cottage style, it sits literally right on Pleasant Bay with deck and stairs leading into the water. In the master bedroom look out across Pleasant Bay before you get out of bed. Full bathroom inside and deligh …see more

from $429 / night

$3000 / week

Book View

from $429 / night

22

South Orleans Vacation cottage rental

Cape Cod / South Orleans

3 5 5 nights min

  • 3 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Lovely, quaint self-catered cottage directly across from Pleasant Bay with spectacular views. Walk across the street to small, sandy Pleasant Bay beach. Three small bedrooms -- one room with double bed, one room with twin beds and one room with a single bed. Full kitch …see more

from $295 / night

$1550 / week

Book View

from $295 / night

25

Vacation home in South Orleans

Cape Cod / South Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
This 4 bedroom, 3 bath home sits on Namequoit River in Orleans and offers a private dock off the backyard area. The first level of the home offers one bedroom with a king sized bed and the second level features three additional bedrooms, two with a queen sized bed and o …see more

from $243 / night

$1701 - $3200 / week

Inquire View

from $243 / night

17

South Orleans Vacation home rental

Cape Cod / South Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
This comfortable 3 bedroom ranch is within close proximity to Little Pleasant Bay. A private walking path brings you to a sandy beach just minutes from your doorstep. The property features three bedrooms and one bath and sleeps up to 6. The first bedroom features a quee …see more

from $158 / night

$1100 - $1600 / week

Inquire View

from $158 / night

26

South Orleans Vacation home rental

Cape Cod / South Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Fall in Love with this expansive 4-BR. Bow Roof House located on a country road in desirable Orleans, within walking distance to Pah Wah landing, where you can launch your boat, kayaks or canoes, or sail to the Outer Beach. The Pah Wah Point hiking trails and a sandy be …see more

from $379 / night

$2650 / week

Inquire View

from $379 / night

22

Home rental in South Orleans

Cape Cod / South Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
This comfortable, updated South Orleans home offers 4 bedrooms and 3 baths with plenty of room to stretch out on your vacation! It features an open layout living/dining area, with a cute sunroom right off the main living space. The first floor boasts an updated, fully e …see more

from $358 / night

$2500 / week

Inquire View

from $358 / night

23

Home rental in South Orleans

Cape Cod / South Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
This roomy and attractively appointed 4 bedroom, 3 bath home offers comfort and privacy in a quiet South Orleans setting. A private dock with boat slip for a dinghy is available at the end of the cul-de-sac. It is a great location for kayaking. Other extras include: a h …see more

from $358 / night

$2500 / week

Inquire View

from $358 / night

18

Vacation home in South Orleans

Cape Cod / South Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
East Egg Associaton Property ID: 52204 Property Name: 2 Ellerslie Road 2017 Season! East Egg community. Private access to association beach on Pleasant Bay which is less than half mile away (access from Ellersie to Carlton to Little Bay Rd. sorry but no parking.) Nice …see more

from $379 / night

$2650 / week

Inquire View

from $379 / night

34

Vacation home in South Orleans

Cape Cod / South Orleans

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Ask about pets
This charming remodeled antique home is only 2/10ths of a mile to a Pleasant Bay beach and a short distance to the five star rated Wequassett Resort. The interior has a brand new kitchen with granite counter tops, stainless steel appliances, wide pine floors and opens u …see more

from $258 / night

$1800 - $2700 / week

Inquire View

from $258 / night

28

South Orleans Vacation home rental

Cape Cod / South Orleans

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Waterfront Home with Large Private Deck and Hot Tub Overlooking Pond JULY 8 -15 PRICE REDUCED TO $2,250!! Peak Summer Weekly Rates: $2,950 - $3,800 (Rents Saturday - Saturday during peak season - Linen Included) If you love nature, privacy and water views this comfortab …see more

from $429 / night

$2000 - $3800 / week

Inquire View

from $429 / night

25

Vacation home in South Orleans

Cape Cod / South Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
This home sits on a bluff overlooking Pleasant Bay with panoramic views from almost every room. With 4 bedrooms and 3 baths, it sleeps 8 comfortably. The property offers one level living with all four bedrooms on the main level. Off the back of the home is a deck area a …see more

from $358 / night

$2500 - $3401 / week

Inquire View

from $358 / night

4

Vacation home in South Orleans

Cape Cod / South Orleans

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Suitable for children age 5+
Six feet of plush lawn separate the MainHouse from the waters of Pleasant Bay. The large garden has plenty of quiet places for reading, relaxing and/or snoozing in the shade or in the sun. Swim or fish from the dock or the nearby beach. Arrangements for a boat mooring …see more

from $1072 / night

$7500 / week

Book View

from $1072 / night

19

Vacation home in South Orleans

Cape Cod / South Orleans

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
ESCAPE from it all to this stunning contemporary, located in South Orleans on a 2 acre lot surrounded by conservation land, one house away from Pleasant Bay. A two minute walk, along one of two scenic paths, leads one to a private association beach on Pleasant Bay. The …see more

from $272 / night

$1900 - $2600 / week

Inquire View

from $272 / night

14

Home rental in South Orleans

Cape Cod / South Orleans

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
9 Woodridge Road (ID# 99912) ~ Bayside 4 Bedroom Home ~ Pleasant Bay Area 2017 Season! Enjoy a Cape Cod vacation. This 4 Bedroom, 2.5 bath home includes a finished basement great for entertaining and access out to the outdoor shower. There are two Bedrooms and a full ba …see more

from $158 / night

$1100 - $1701 / week

Inquire View

from $158 / night

1