Find short term rentals in Orleans, MA at the best prices

628 available short term rental offers

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Orleans, MA short term rentals
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Best Short term and Weekly rentals in Orleans, MA

Best family friendly Orleans, MA Short term rentals

Among the 628 accommodations in Orleans, MA, here are the 4 best family friendly rentals

Exceptional Mid-cape Oasis With Many Amenities! - Orleans, MA
9.6 23 reviews
Orleans, MA
25/06 – 30/06
$2010/nighttotal: $10050 (5 )

Exceptional Mid-cape Oasis With Many Amenities!

4 2
apartment , Harwich
This apartment is ideally located in Harwich, just 16km from the charming town of Chatham and 48km from Provincetown. The property has excellent user, location, and cleanliness ratings, indicating a high-quality stay.
This spacious home has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. The apartment offers a range of amenities, including a swimming pool, jacuzzi, terrace, garden, and parking, ensuring a relaxing and enjoyable stay.
Charming Retreat Near The Ocean With W/d, Games, & Trails - Orleans, MA
10 4 reviews
Orleans, MA
25/06 – 30/06
$1450/nighttotal: $7250 (5 )

Charming Retreat Near The Ocean With W/d, Games, & Trails

5 2
apartment , Eastham
This five-bedroom Eastham holiday home offers direct access to the Cape Cod National Seashore and is a short walk to the beach and the Cape Cod Rail Trail, ideal for cycling and walking.
This 190 square metre property accommodates up to ten guests with four bathrooms, a well-equipped kitchen including a dishwasher, and a screened porch, alongside outdoor games and a deck with a grill for entertainment.
New 2026 Charming Home Just Over A Mile To Coast G - Orleans, MA
Orleans, MA
25/06 – 30/06
$1410/nighttotal: $7050 (5 )

New 2026 Charming Home Just Over A Mile To Coast G

1 2
apartment , Eastham
This Eastham holiday let offers a prime location, a short walk from the Cape Cod National Seashore visitor centre and approximately 2.4 kilometres from Coast Guard Beach.
This family-friendly holiday home accommodates eight guests across four bedrooms and features two bathrooms, air conditioning, a garden, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
2nd Floor Cottage, Oceanview, Deck, Shared Grill, & Outdoor Shower - Orleans, MA
9.6 38 reviews
Orleans, MA
03/08 – 07/08
$984/nighttotal: $3936 (4 )

2nd Floor Cottage, Oceanview, Deck, Shared Grill, & Outdoor Shower

3 3
apartment , Orleans
This upper-level Cape Cod cottage in East Orleans offers direct, walkable access to Nauset Beach, eliminating parking issues, and is a 1.6 to 2.4 kilometre drive from the Cape Cod Rail Trail.
This 103 square metre flat, accommodating up to six guests across three bedrooms and one bathroom, features a kitchen with a fridge and microwave, air conditioning, a terrace/balcony, and is situated a short walk from Orleans shops, dining, and attractions like the Orleans Bowling Centre.

Best Orleans, MA lodging with a balcony

Book Eastham, Plenty Of Room For Entire Family! - Orleans, MA
9.6 11 reviews
Orleans, MA
03/08 – 07/08
$1426/nighttotal: $5704 (4 )

Book Eastham, Plenty Of Room For Entire Family!

3 3
apartment , Eastham
This Eastham apartment is situated in a quiet residential area, 1.6 kilometres from Nauset Light Beach and close to bayside beaches suitable for families.
This 167 square metre residence accommodates up to six guests across three bedrooms and two bathrooms, featuring a fully equipped kitchen, a separate dining room, a downstairs entertainment area, and extensive outdoor space with a gas grill and firepit, all supported by WiFi and parking for four vehicles.
Ship's Knees Inn - Orleans, MA
9.2 50 reviews
Orleans, MA
25/06 – 30/06
$761/nighttotal: $3805 (5 )

Ship's Knees Inn

1 2
B&B , Orleans
The Ship's Knees Inn is a charming bed and breakfast located just a five-minute walk from Nauset Beach in Orleans, offering easy access to the beautiful sandy shores and the Cape Cod Rail Trail. The inn has received excellent ratings for its cleanliness, location and overall experience.
The rooms are decorated in a traditional Cape Cod style, creating a welcoming and authentic atmosphere. Guests can enjoy a continental breakfast, relax on the terrace with a fire pit, take a dip in the seasonal pool, or explore the nearby Cape Cod Museum of Natural History.
Renovated 2nd-floor Corner Unit, New Interiors. Beach, Parking Passes On Us. - Orleans, MA
10 1 review
Orleans, MA
25/06 – 30/06
$479/nighttotal: $2395 (5 )

Renovated 2nd-floor Corner Unit, New Interiors. Beach, Parking Passes On Us.

1 2
apartment , Brewster
This recently renovated one-bedroom flat is located within the Ocean Edge resort in Brewster, offering convenient access to Cape Cod Beaches and Nickerson State Park, just 1.6 kilometres away.
This apartment accommodates up to four guests with a queen bed and a sleeper sofa, featuring a fully equipped kitchen, air conditioning, a balcony, garden access, and dedicated parking, with beach chairs and towels provided for your use.
Gorgeous Woodland Home With Deck & Firepit - Walk To Ocean Bluffs & Rail Trail - Orleans, MA
Orleans, MA
03/08 – 07/08
$1059/nighttotal: $4236 (4 )

Gorgeous Woodland Home With Deck & Firepit - Walk To Ocean Bluffs & Rail Trail

3 3
apartment , Eastham
This Eastham residence, a detached house, offers a secluded woodland setting with wildlife and is situated less than 1 kilometre from ocean bluffs and just over 1.6 kilometres from Nauset Light Beach, also being conveniently located half a kilometre from the Cape Cod Rail Trail.
This spacious 218 square metre property boasts three bedrooms and three bathrooms, accommodating up to four guests, and features unique reclaimed American chestnut beams, expansive outdoor space including a deck and firepit, a sunroom, and central air conditioning downstairs with mini-splits upstairs.

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Best Orleans, MA lodging with a kitchen

Sunny Orleans Cottage Near Skaket Beach! 1929 - Orleans, MA
Orleans, MA
25/06 – 30/06
$614/nighttotal: $3070 (5 )

Sunny Orleans Cottage Near Skaket Beach! 1929

2 2
apartment , Orleans
This Orleans cottage is located in a quiet neighbourhood, just a short distance from the popular Skaket Beach.
This property offers accommodation for up to five guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen, a three-season sunroom, a finished basement with a ping pong table, a private deck with a gas grill, and an enclosed outdoor shower.
Peaceful Waterfront Cottage Escape - Orleans, MA
Orleans, MA
25/06 – 30/06
$702/nighttotal: $3510 (5 )

Peaceful Waterfront Cottage Escape

2 2
cottage , Eastham
This Eastham holiday home is located on Town Cove, offering direct water access and a private dock, with the Cape Cod National Seashore just 1.4 kilometres away and the Cape Cod Rail Trail 1.5 kilometres distant.
This two-bedroom, two-bathroom cottage spans 121 square metres, accommodates four guests, and includes a kitchen with a fridge and microwave, air conditioning, Wi-Fi, parking, and complimentary daily tickets to local attractions through the Xplorie partnership.
Relax And Refresh In Eastham - Orleans, MA
9.8 9 reviews
Orleans, MA
25/06 – 30/06
$702/nighttotal: $3510 (5 )

Relax And Refresh In Eastham

1 2
apartment , Eastham
This Eastham flat offers a prime location, a mere 800 metres from First Encounter Beach and 1.6 kilometres from Coast Guard Beach.
This newly available coastal retreat sleeps up to six guests across two bedrooms and a loft, featuring an open-plan living, dining, and kitchen area with air conditioning, Wi-Fi, and off-street parking.
Beautifully Renovated Second-floor Condo - Orleans, MA
Orleans, MA
25/06 – 30/06
$386/nighttotal: $1930 (5 )

Beautifully Renovated Second-floor Condo

1 2
apartment , Brewster
This newly renovated one-bedroom flat in Brewster is located within the Ocean Edge Resort, offering proximity to the Cape Cod Bay shoreline.
This accommodation provides a queen bed and sleeper sofa for up to four guests, a fully equipped kitchen with new appliances, a recently updated bathroom, and year-round comfort with heating and air conditioning, all complemented by complimentary parking.

Best Orleans, MA lodging with laundry available

Spacious Harwich Haven Near Round Cove (1116) - Orleans, MA
9.4 8 reviews
Orleans, MA
25/06 – 30/06
$742/nighttotal: $3710 (5 )

Spacious Harwich Haven Near Round Cove (1116)

3 2
apartment , Harwich
This detached house in Harwich is located on a quiet cul-de-sac, 800 metres from Round Cove on Pleasant Bay, offering convenient access to Chatham and Orleans.
The property features four bedrooms accommodating up to eight guests, a well-equipped kitchen, a TV room, a large living room with deck access, a garden with an enclosed outdoor shower, and a gas barbecue, with nearby activities including sailing, surfing, fishing, and cycling.
Large Family Home & Yard: Your Cape Cod Getaway - Orleans, MA
9.5 4 reviews
Orleans, MA
25/06 – 30/06
$750/nighttotal: $3750 (5 )

Large Family Home & Yard: Your Cape Cod Getaway

1 2
apartment , Eastham
This Eastham holiday home enjoys a superb location, less than 1.6km from the Cape Cod Rail Trail, Fort Hill Trail, and Great Pond Beach, with First Encounter Beach (3.2km) and Nauset Light Beach (6.4km) also within easy reach.
Sleeping eight, this three-bedroom, two-bathroom property boasts a full kitchen, air conditioning, Wi-Fi, a private garden with barbecue and fire pit, plus bikes and beach toys; a unique basement 'Connie's Pub' adds a quirky touch.
Harwich Escape – Deck, Firepit & Near Beaches - Orleans, MA
Orleans, MA
25/06 – 30/06
$1005/nighttotal: $5025 (5 )

Harwich Escape – Deck, Firepit & Near Beaches

3 2
apartment , Harwich
This Harwich Port flat is situated 0.7 kilometres from Pleasant Road beach, with Harwich Port's shops and eateries a short distance away, and offers convenient access to the Cape Cod Rail Trail for cycling and walking.
This property accommodates up to eight guests across three bedrooms and two bathrooms, boasting a garden with a deck, patio, gas grill and firepit, an outdoor shower, and a well-equipped kitchen with full-size appliances, plus air conditioning and Wi-Fi for comfort.
Cozy Cottage By Molls Pond 2409 - Orleans, MA
Orleans, MA
25/06 – 30/06
$602/nighttotal: $3010 (5 )

Cozy Cottage By Molls Pond 2409

2 2
apartment , Eastham
This two-bedroom cottage is situated in a tranquil Eastham neighbourhood, offering swift access to Route 6 and proximity to the Atlantic and Cape Cod Bay beaches, with Molls Pond just 400 metres away for fishing and kayaking.
This holiday let accommodates up to four guests and features a garden, outdoor shower, and a porch with dining facilities, alongside an open-plan living area with a television and air conditioning, plus a fitness centre for guest use.
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