Marthas Vineyard Cottages - Vacation Rentals in South Side

Premium Furnished 2B 1.5B Home Monthly Stay in Newton From US $306
         

Charming 3BR, 1BA Near Heart of Boston! From US $340
         

|
9.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Crescent Suites Hotel From US $160
         

|
9.6 (1163 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Spacious Private Retreat Near Downtown Boston! From US $243
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Luxury Apt with Rooftop Terrace and Pool From US $330
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Harvard House: Make Your 2025 Family Gathering Unforgettable" From US $972
         

Remodeled Townhouse close to Boston From US $414
         

9.8 (46 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Luxury large house minutes to Cambridge and Boston From US $1,096
         

Luxury Places to Stay in South Side

Over 194+ Luxury Places to Stay in or Near South Side
Ultra-Luxurious Home near Boston (Pet-Friendly) From US $1,248
         

Totally Renovated 3Br Apartment From US $967
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Harvard House-The Gathering Place From US $950
         

Cozy&Spacious 6Br home in Newton + Parking From US $908
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Cozy&Spacious 6Br home in Newton From US $896
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Boston`s Luxury Home: Pet-Friendly, 4BR, Sleeps 10 From US $887
         

9.2 (14 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
216-5 Entire studio private entry From US $800
         

New
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

Top-Rated Vacation Rentals with a Pool in South Side

Over 51+ Top-Rated Vacation Rentals with a Pool in or Near South Side
Contemporary Room | Free Breakfast, Parking & Gym Access From US $236
         

Hampton Inn & Suites Boston/Waltham From US $141
         

|
9.4 (1695 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Courtyard by Marriott Boston Waltham From US $127
         

|
9.2 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Fairfield Inn & Suites by Marriott Boston Waltham From US $140
         

|
9.0 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Residence Inn by Marriott Boston Waltham From US $145
         

|
9.0 (838 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Westin Waltham-Boston From US $144
         

|
8.8 (1092 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in South Side

Over 81+ Pet-Friendly Vacation Rentals in or Near South Side
Totally Renovated 3Br Apartment From US $502
         

|
7.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Beautiful new apartment 2bed/2bath Waltham From US $354
         

9.4 (30 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Gorgeous with a back yard and parking pet friendly on the heart of Waltham From US $372
         

Cozy house close to Brandeis, Bentley, Moody St From US $473
         

Blueground | Bleachery, pool, nr Charles River From US $508
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Newly Renovated 3Br Apt Near Boston + Parking From US $487
         

New
Apartment
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens
Blueground | Bleachery, pool, nr Charles River From US $229
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool

Large Vacation Homes & Villas in South Side

Over 11+ Large Vacation Homes & Villas in or Near South Side
Studio remodeled.! From US $124
         

New
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Waterfront 5-bedroom house in terrific Newtonville From US $992
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Spacious 5-bedroom house with theatre and gym From US $3,445
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Entire Cozy House near Moody St, Bentley, Brandeis From US $620
         

8.4 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in South Side

Over 64+ Wheelchair Accessible Vacation Homes in or Near South Side
Hampton Inn & Suites Boston/Waltham From US $294
         

|
8.8 (762 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Holiday Inn Express Boston - Waltham by IHG From US $123
         

9.2 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Blueground | Bleachery, pool, nr Charles River From US $211
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Blueground | Bleachery, pool, nr Charles River From US $209
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Blueground | Bleachery, pool, nr Charles River From US $106
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Beautiful New Apartment near Moody St/Commuter Rail Into Boston From US $425
         

9.2 (54 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

South Side Vacation Rentals and Airbnb Places to Stay Under $200

Over 66+ South Side Vacation Rentals and Airbnb Places to Stay Under $200
Historic Private Auburndale Retreat Near Boston! From US $133
         

9.6 (14 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Hilton Garden Inn Boston/Waltham From US $109
         

|
8.8 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Private Auburndale Getaway Minutes from Boston! From US $184
         

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Private Studio remodeled…! From US $135
         

New
Condo
  • Air Conditioner
  • Parking
  • Security/Safety

Instantly Bookable Vacation Homes in South Side

Over 72+ Instantly Bookable Vacation Homes in or Near South Side
Charming Townhouse 12 minutes to Boston From US $395
         

9.6 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Lower-level, a Double bed, shared bath & kitchen From US $89
         

New
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Experience Classic Charm in a Cozy 115-Year-Old Colonial From US $352
         

Spacious 4BR Stay Ideal for Groups! From US $703
         

8.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About South Side Vacation Rentals

With more than 203 South Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Marthasvineyardcottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in South Side.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Marthasvineyardcottages South Side, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in South Side. Places to stay near South Side are 685.05 ft² on average, with prices averaging $339 a night.

Marthasvineyardcottages makes it easy and safe to find and compare vacation rentals in South Side with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in South Side

Type Count
Holiday Apartments 81
Vacation Homes 61
Hotels with Suites 44
Villas 2
Others 1

Use these Quick Filters to Find a Vacation Rental in South Side

Pro Tip: Marthasvineyardcottages makes it easy to compare the best listings on Marthasvineyardcottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Marthasvineyardcottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in South Side.

Weather in South Side

View the weather forecast for South Side before booking your South Side Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay Near South Side, MA


South Side Vacation Rental Frequently Asked Questions

How many vacation rentals are available in South Side?

Currently, the total number of properties listed in 2026 is over 203 in the South Side area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in South Side.