Sailings Canada - Vacation Rentals in Wellington Hill

Newly renovated pet friendly apt by parks and train! From US $341
         

8.0 (36 Reviews)
Apartment
  • Air Conditioner
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  • Pet Friendly
Milton Cozy Home From US $1,212
         

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New
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Homestay In Fields Corner Area Boston From US $67
         

8.8 (36 Reviews)
Bed & Breakfast
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  • Restaurant
  • Guest Services
City's Hippest Neighborhood. n From US $965
         

10.0 (102 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
🎖The Ashmont Suite - Close to Subway + Downtown🎖 From US $538
         

Luxury Places to Stay in Wellington Hill

Over 546+ Luxury Places to Stay in or Near Wellington Hill
Clean, Contemporary Duplex | Sleeps 17 From US $2,323
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
New Luxury Renovation | Near T From US $2,276
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Spacious, New Renovation | Near T From US $2,070
         

10.0 (24 Reviews)
House
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  • TV
  • Security/Safety
Boston Luxury Suits Cottage for up to 24 guests! From US $2,030
         

10.0 (2 Reviews)
House
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  • Parking
  • Pet Friendly
Spacious 6BR 2unit near Downtown From US $1,715
         

9.0 (4 Reviews)
House
  • Air Conditioner
  • Designated Smoking Area
  • TV
5BR World Cup Stay Sleeps 16 Parking Walk to train From US $1,655
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Top-Rated Vacation Rentals with a Pool in Wellington Hill

Over 5+ Top-Rated Vacation Rentals with a Pool in or Near Wellington Hill
Ramada by Wyndham Boston From US $122
         

6.8 (1680 Reviews)
Hotel
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  • Pool
Ramada by Wyndham Boston From US $132
         

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6.5 (3189 Reviews)
Hotel
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  • Pet Friendly

Pet-Friendly Vacation Rentals in Wellington Hill

Over 175+ Pet-Friendly Vacation Rentals in or Near Wellington Hill
Spacious, Comfy Colonial, minutes to Boston and highways From US $764
         

10.0 (31 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
558-1 Boston - Spacious & Modern 3BR near Franklin Park From US $652
         

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10.0 (3 Reviews)
Apartment
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  • Pet Friendly
Budget-Friendly Basement 2BR Retreat From US $340
         

10.0 (20 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
10-Spacious 5BR apt with gym, games room in the attic From US $502
         

10.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern 3BR nest near Franklin Park 558/2 From US $331
         

10.0 (16 Reviews)
Apartment
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  • Parking
  • Pet Friendly
Spacious 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View From US $820
         

Modern Condo First Floor Boston From US $590
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Large Vacation Homes & Villas in Wellington Hill

Over 146+ Large Vacation Homes & Villas in or Near Wellington Hill
Mid-Century Glam Retreat, Near T From US $914
         

10.0 (16 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
60-2 3BR Boston - Modern Apt near Franklin Park From US $652
         

Two story Cozy of Boston Home. From US $645
         

Peaceful Milton Getaway- Trails & City Nearby From US $1,326
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
5BR World Cup Stay Sleeps 16 Parking Walk to train easy access to Stadium From US $1,208
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Modern Boston Condo | near T From US $1,160
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Wellington Hill

Over 35+ Wheelchair Accessible Vacation Homes in or Near Wellington Hill
Business Center + Breakfast | Near Central Boston From US $357
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Best Western Adams Inn Quincy-Boston From US $519
         

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7.0 (779 Reviews)
Hotel
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  • Parking
  • Pet Friendly
Best Western Adams Inn Quincy-Boston From US $140
         

7.6 (1120 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Cozy Boston Home | Near T From US $302
         

9.4 (3 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Spacious Boston Home, Near T From US $306
         

9.0 (8 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Stylish Boston Home, Near T From US $313
         

New
Condo
  • Air Conditioner
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  • Wheelchair Accessible

Wellington Hill Vacation Rentals and Airbnb Places to Stay Under $200

Over 112+ Wellington Hill Vacation Rentals and Airbnb Places to Stay Under $200
Boston Historic Lower Mills From US $108
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Homestay Near Near Savin Hill Area From US $107
         

7.2 (9 Reviews)
Bed & Breakfast
  • Bedding/Linens
  • Fireplace/Heating
  • Guest Services
🎖The Boiler Room - Close to Subway & Downtown🎖 From US $186
         

Delightful 2-bedroom house in Milton From US $199
         

New
House
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  • Security/Safety
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A One Room Studio in a Quiet & Convenient Location From US $185
         

Instantly Bookable Vacation Homes in Wellington Hill

Over 303+ Instantly Bookable Vacation Homes in or Near Wellington Hill
Charming Tree Top Victorian - Two Bedroom Retreat From US $486
         

10.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Charming Boston-Fairmont Hills Apartment From US $345
         

10.0 (15 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Luxury 3brm/1bath Duplex in JP From US $629
         

10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Lg suite for up to 8 ppl/2 floor From US $552
         

10.0 (12 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
The Arbor Retreat From US $955
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Under the Sun Apartment From US $623
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

About Wellington Hill Vacation Rentals

With more than 555 Wellington Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Sailings 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 Wellington Hill.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Sailings Wellington Hill, 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 Wellington Hill. Places to stay near Wellington Hill are 708.69 ft² on average, with prices averaging $474 a night.

Sailings makes it easy and safe to find and compare vacation rentals in Wellington Hill 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 Wellington Hill

Type Count
Holiday Apartments 328
Vacation Homes 137
B&B 9
Hotels with Suites 6

Use these Quick Filters to Find a Vacation Rental in Wellington Hill

Pro Tip: Sailings makes it easy to compare the best listings on Sailings homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sailings 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 Wellington Hill.

Weather in Wellington Hill

View the weather forecast for Wellington Hill before booking your Wellington Hill 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 Wellington Hill, MA


Wellington Hill Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Wellington Hill?

Currently, the total number of properties listed in 2026 is over 555 in the Wellington Hill area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Wellington Hill.