27+ Vacation Rentals Near Massachusetts |
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Cruise And Resorts - Vacation Rentals in Massachusetts

Boston Harbor Yacht, AC/Heat, Walk to North End WiFi From US $445
         

9.6 (144 Reviews)
Boat Rental
Boston Harbor Yacht, AC/Heat, Walk to North End WiFi
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lakefront Otis Home with Stunning Views and Boats! From US $346
         

|
10.0 (5 Reviews)
House
Lakefront Otis Home with Stunning Views and Boats!
  • Parking
  • View
  • Ocean View

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Houseboat in Boston Harbor Wifi A/C/Heat Be rocked to sleep From US $444
         

9.8 (201 Reviews)
Boat Rental
Houseboat in Boston Harbor Wifi A/C/Heat Be rocked to sleep
  • Air Conditioner
  • Parking
  • Pet Friendly

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"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail From US $697
         

10.0 (120 Reviews)
Boat Rental
"Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail
  • Air Conditioner
  • Parking
  • TV

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Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard From US $455
         

10.0 (241 Reviews)
Boat Rental
Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard
  • Air Conditioner
  • Parking
  • TV

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Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by From US $455
         

10.0 (57 Reviews)
Boat Rental
Best of Boston Houseboat Heat/AC in Boston Harbor Suite2 -Freedom Trail close by
  • Air Conditioner
  • Parking
  • TV

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Endless Summer: Oceanside Views From US $549
         

10.0 (41 Reviews)
Boat Rental
Endless Summer: Oceanside Views
  • Air Conditioner
  • Parking
  • TV

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Fun houseboat. Walk to Boston attractions WIFI From US $417
         

9.8 (89 Reviews)
Boat Rental
Fun houseboat. Walk to Boston attractions WIFI
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury Places to Stay in Massachusetts

Over 10000+ Luxury Places to Stay in or Near Massachusetts
2 BR, Modern Main House, 1000 feet of private beach, AC, WiFi, Gym From US $21,223
         

New
House
2 BR, Modern Main House, 1000 feet of private beach, AC, WiFi, Gym
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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One Block From Surf Drive Beach. Walk to town and ferry. 2 parking spots From US $20,814
         

10.0 (14 Reviews)
Condo
One Block From Surf Drive Beach. Walk to town and ferry. 2 parking spots
  • Air Conditioner
  • Parking
  • TV

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7-Bed Rooms, Modern Main House, 1000 ft private beach, AC, Fast WiFi, Smart TV From US $17,172
         

New
House
7-Bed Rooms, Modern Main House, 1000 ft private beach, AC, Fast WiFi, Smart TV
  • Air Conditioner
  • Parking
  • TV

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Close to TD Garden | Free Breakfast & Wi-Fi From US $16,186
         

New
Hotel
Close to TD Garden | Free Breakfast & Wi-Fi
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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New Boutique King Suite Escape l Downtown l Backyard From US $12,546
         

New
Hotel
New Boutique King Suite Escape l Downtown l Backyard
  • Air Conditioner
  • Bedding/Linens
  • Wellness Facilities

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New Boutique Ocean Escape l Downtown l King Bed l ADA From US $12,408
         

New
Hotel
New Boutique Ocean Escape l Downtown l King Bed l ADA
  • Child Friendly

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Stunning Miacomet Beach House w/Pool, Hot tub, Sauna & Jeep Available to Rent! From US $12,343
         

New
House
Stunning Miacomet Beach House w/Pool, Hot tub, Sauna & Jeep Available to Rent!
  • Air Conditioner
  • Pet Friendly
  • Pool

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Steps to Cambridge Crossing | Free Breakfast From US $11,675
         

New
Hotel
Steps to Cambridge Crossing | Free Breakfast
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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Find More Massachusetts Villas, Resorts, & Rentals on BedroomVillas

Top-Rated Vacation Rentals with a Pool in Massachusetts

Over 4393+ Top-Rated Vacation Rentals with a Pool in or Near Massachusetts
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant! From US $525
         

10.0 (291 Reviews)
Cottage
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Steps to the Ocean! Perfect Location! From US $199
         

10.0 (237 Reviews)
Cottage
Steps to the Ocean! Perfect Location!
  • Air Conditioner
  • Parking
  • Pool

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Luxurious Harbor View "Millie" Cottage! Walk & bike to everything! From US $667
         

10.0 (236 Reviews)
Cottage
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything! From US $534
         

10.0 (233 Reviews)
Cottage
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Village Inn Cape Cod From US $235
         

|
10.0 (224 Reviews)
Bed & Breakfast
The Village Inn Cape Cod
  • Air Conditioner
  • Parking
  • Pool

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4 Bedroom LUX House/with Pool Next Door From US $405
         

10.0 (212 Reviews)
House
4 Bedroom LUX House/with Pool Next Door
  • Air Conditioner
  • Parking
  • Pool

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The Clearing - Quiet - Close To Nature From US $144
         

10.0 (212 Reviews)
Cottage
The Clearing - Quiet - Close To Nature
  • Parking
  • Pool
  • View

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LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches From US $930
         

10.0 (178 Reviews)
House
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pet-Friendly Vacation Rentals in Massachusetts

Over 9663+ Pet-Friendly Vacation Rentals in or Near Massachusetts
Harmony Medical Suites on Canal From US $210
         

|
10.0 (1 Review)
Apartment
Harmony Medical Suites on Canal
  • Air Conditioner
  • Parking
  • Pet Friendly

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New, dog-friendly 5-bed home. Steps to Keyes Beach, Main Street, and Harbor! From US $600
         

10.0 (152 Reviews)
House
New, dog-friendly 5-bed home. Steps to Keyes Beach, Main Street, and Harbor!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Dusk Suite at The Hygge House, Dusk Suite at The Hygge House From US $165
         

8.6 (4 Reviews)
Apartment
Dusk Suite at The Hygge House, Dusk Suite at The Hygge House
  • Air Conditioner
  • Parking
  • Pet Friendly

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#Game Room, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central ACHeat From US $399
         

10.0 (130 Reviews)
House
#Game Room, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central ACHeat
  • Air Conditioner
  • Parking
  • Pet Friendly

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Ocean Views From Every Room, Beach 30 Seconds Away! From US $984
         

10.0 (113 Reviews)
House
Ocean Views From Every Room, Beach 30 Seconds Away!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Relaxing Lakefront Dog Friendly 4 Bedroom Home Close to Town, Beaches & Shopping From US $515
         

10.0 (58 Reviews)
House
Relaxing Lakefront Dog Friendly 4 Bedroom Home Close to Town, Beaches & Shopping
  • Air Conditioner
  • Parking
  • Pet Friendly

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Oceanfront Escape house on SeaView Beach, Dog-Friendly! From US $617
         

9.8 (124 Reviews)
House
Oceanfront Escape house on SeaView Beach, Dog-Friendly!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Plum Island Guest Cottage With Water View From US $167
         

9.8 (66 Reviews)
Cottage
Plum Island Guest Cottage With Water View
  • Air Conditioner
  • Parking
  • Pet Friendly

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See More Pet-Friendly Vacation Rentals in Massachusetts on PetFriendly.io

Large Vacation Homes & Villas in Massachusetts

Over 5453+ Large Vacation Homes & Villas in or Near Massachusetts
The Upton From US $129
         

|
6.5 (13 Reviews)
Apartment
The Upton
  • Air Conditioner
  • Breakfast
  • Internet

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Located Steps Away To Main Street And .7 Miles From Surf Drive Beach From US $288
         

10.0 (212 Reviews)
House
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
  • Air Conditioner
  • Parking
  • TV

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WATERFRONT home close to Downtown Chatham! From US $1,105
         

10.0 (8 Reviews)
House
WATERFRONT home close to Downtown Chatham!
  • Air Conditioner
  • Parking
  • Pet Friendly

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4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi From US $290
         

10.0 (163 Reviews)
House
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
  • Parking
  • TV
  • View

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BEAUTIFUL and PRIVATE OSTERVILLE HOME, LARGE GAME ROOM, AC,PARKING From US $1,016
         

10.0 (88 Reviews)
House
BEAUTIFUL and PRIVATE OSTERVILLE HOME, LARGE GAME ROOM, AC,PARKING
  • Air Conditioner
  • Parking
  • TV

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Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026! From US $1,277
         

10.0 (71 Reviews)
House
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
  • Air Conditioner
  • Parking
  • TV

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Live the Good Life! Heated Pool, Walk to Ocean Beaches, Sleeps 12 in 6 rooms From US $817
         

10.0 (71 Reviews)
House
Live the Good Life! Heated Pool, Walk to Ocean Beaches, Sleeps 12 in 6 rooms
  • Air Conditioner
  • Parking
  • Pool

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Modern And Spacious Berkshires Retreat 5 bdrm 3 bath From US $477
         

10.0 (60 Reviews)
House
Modern And Spacious Berkshires Retreat 5 bdrm 3 bath
  • Air Conditioner
  • Parking
  • TV

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Wheelchair Accessible Vacation Homes in Massachusetts

Over 3734+ Wheelchair Accessible Vacation Homes in or Near Massachusetts
Bird Hill Farm From US $89
         

10.0 (2 Reviews)
Bed & Breakfast
Bird Hill Farm
  • Air Conditioner
  • Parking
  • Pet Friendly

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Boston Marriott Custom House ~ Downtown Suite with views of the city and harbor From US $1,028
         

10.0 (11 Reviews)
Villa
Boston Marriott Custom House ~ Downtown Suite with views of the city and harbor
  • Air Conditioner
  • Parking
  • TV

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Howarth House B&B From US $235
         

|
10.0 (112 Reviews)
Bed & Breakfast
Howarth House B&B
  • Air Conditioner
  • Parking
  • Pool

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Furnished Delx Studio w/Full Kitchen & Fast WiFi | Boston From US $147
         

10.0 (1 Review)
Apartment
Furnished Delx Studio w/Full Kitchen & Fast WiFi | Boston
  • Air Conditioner
  • Parking
  • TV

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Spacious 3BR in Heart of Downtown Boston! Walk-Everywhere! From US $616
         

10.0 (58 Reviews)
Apartment
Spacious 3BR in Heart of Downtown Boston! Walk-Everywhere!
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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Bright & Spacious Loft Steps to the Freedom Trail From US $337
         

10.0 (52 Reviews)
Condo
Bright & Spacious Loft Steps to the Freedom Trail
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1 From US $303
         

10.0 (42 Reviews)
Condo
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
  • Air Conditioner
  • Parking
  • Pool

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Executive Waterfront Luxury Estate 6000 Sqft; Heated Pool; Elevator From US $2,410
         

10.0 (41 Reviews)
House
Executive Waterfront Luxury Estate 6000 Sqft; Heated Pool; Elevator
  • Air Conditioner
  • Parking
  • Pool

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Massachusetts Vacation Rentals and Airbnb Places to Stay Under $200

Over 4530+ Massachusetts Vacation Rentals and Airbnb Places to Stay Under $200
Bluebird Suites near MIT From US $143
         

|
8.0 (1 Review)
Apartment
Bluebird Suites near MIT
  • Air Conditioner
  • Parking
  • Pet Friendly

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Adorable cottage on Cape Cod's historic Rt 6A From US $193
         

10.0 (144 Reviews)
Cottage
Adorable cottage on Cape Cod's historic Rt 6A
  • Air Conditioner
  • Parking
  • TV

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Granville House From US $194
         

|
10.0 (94 Reviews)
Bed & Breakfast
Granville House
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Steps To Bay at Campground Beach, A/C, Heat,Wifi, Outdoor Shower, Gas Grill From US $193
         

10.0 (43 Reviews)
Cottage
Steps To Bay at Campground Beach, A/C, Heat,Wifi, Outdoor Shower, Gas Grill
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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Steps to Cooks Brook Beach! A/C, Heat, Wifi, Outdoor Shower, Gas Grill From US $198
         

9.8 (47 Reviews)
Cottage
Steps to Cooks Brook Beach! A/C, Heat, Wifi, Outdoor Shower, Gas Grill
  • Air Conditioner
  • Parking
  • TV

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Linny's Lakeview Cottage - updated From US $197
         

10.0 (65 Reviews)
House
Linny's Lakeview Cottage - updated
  • Air Conditioner
  • Parking
  • TV

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Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating From US $176
         

9.6 (235 Reviews)
Cabin
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
  • Air Conditioner
  • Parking
  • Pet Friendly

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Has pool-1/2 mile to beach-Pilgrim Acres Village- Private Condo community From US $170
         

8.8 (10 Reviews)
Cottage
Has pool-1/2 mile to beach-Pilgrim Acres Village- Private Condo community
  • Air Conditioner
  • Parking
  • Pool

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Instantly Bookable Vacation Homes in Massachusetts

Over 15146+ Instantly Bookable Vacation Homes in or Near Massachusetts
Best Patio on Commercial-Tropical Garden-Prime Location From US $280
         

10.0 (146 Reviews)
Condo
Best Patio on Commercial-Tropical Garden-Prime Location
  • Air Conditioner
  • Parking
  • TV

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New Boutique King Suite Escape l Downtown l Backyard From US $10,000
         

New
Hotel
New Boutique King Suite Escape l Downtown l Backyard
  • Air Conditioner
  • Bedding/Linens
  • Wellness Facilities

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WaterViews Overlooking Gloucester Inner Harbor/Sunroom/Deck/Walk to Town/AC From US $471
         

10.0 (142 Reviews)
House
WaterViews Overlooking Gloucester Inner Harbor/Sunroom/Deck/Walk to Town/AC
  • Air Conditioner
  • Parking
  • TV

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PRIVATE BEACH, 2 min walk. WIFI, AC, sunny/clean. New Kitchen & screened porch. From US $616
         

10.0 (139 Reviews)
House
PRIVATE BEACH, 2 min walk. WIFI, AC, sunny/clean. New Kitchen & screened porch.
  • Air Conditioner
  • Parking
  • TV

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BEAUTIFUL COTTAGE ON ORANGE STREET, WALK TO MAIN! PERFECT FOR FAMILY VACATION! From US $668
         

10.0 (133 Reviews)
Cottage
BEAUTIFUL COTTAGE ON ORANGE STREET, WALK TO MAIN! PERFECT FOR FAMILY VACATION!
  • Air Conditioner
  • Parking
  • TV

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Front Row! West End. Now 2 new bathrooms! Boatslip/Mussel Beach Gym/Sleeps 6! From US $360
         

10.0 (130 Reviews)
Condo
Front Row! West End. Now 2 new bathrooms! Boatslip/Mussel Beach Gym/Sleeps 6!
  • Air Conditioner
  • Parking
  • TV

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Luxury Accommodations in Quiet Seaside Village From US $240
         

10.0 (130 Reviews)
Apartment
Luxury Accommodations in Quiet Seaside Village
  • Air Conditioner
  • Parking
  • TV

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Save now for Stroll and winter! Charming cottage, close to lower Main Street. From US $294
         

10.0 (118 Reviews)
Cottage
Save now for Stroll and winter! Charming cottage, close to lower Main Street.
  • Air Conditioner
  • Parking
  • TV

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About Massachusetts Vacation Rentals

With more than 27 Massachusetts vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Cruiseandresorts 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 Massachusetts.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruiseandresorts Massachusetts, 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 Massachusetts. Places to stay near Massachusetts are 242.11 ft² on average, with prices averaging $528 a night.

Cruiseandresorts makes it easy and safe to find and compare vacation rentals in Massachusetts 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 Massachusetts

Type Count
Vacation Homes 1

Use these Quick Filters to Find a Vacation Rental in Massachusetts

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

Weather in Massachusetts

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

December - February
High 45°F       Low 20°F
March - May
High 63°F       Low 22°F
June - August
High 80°F       Low 57°F
September - November
High 74°F       Low 30°F

Top Attractions Around Massachusetts, US

Cruiseandresorts offers a large selection of top attractions around Massachusetts. Research things to do on your vacation before you visit Massachusetts.


Fenway Park Boston University Harvard University TD Garden Boston Common Faneuil Hall Marketplace Boston Convention and Exhibition Center Gillette Stadium New England Aquarium Northeastern University Boston Museum of Fine Arts Copley Square Harvard Square Massachusetts General Hospital Museum of Science Hynes Convention Center University of Massachusetts-Amherst Massachusetts Institute of Technology Copley Place Boston Children's Museum Xfinity Center Salem Witch Museum Boston College Black Falcon Cruise Terminal Boston Opera House Jiminy Peak Mountain Resort Boston Harbor Quincy Market Prudential Tower Old Sturbridge Village

Other Places to Stay Near Massachusetts, US


Barnstable County 8,230 Properties Cape Cod 8,163 Properties Boston 4,573 Properties Suffolk County 2,249 Properties Middlesex County 1,463 Properties North Shore 1,309 Properties Essex County 1,297 Properties Dukes County 1,106 Properties Martha's Vineyard 1,105 Properties Berkshire County 1,017 Properties The Berkshires 1,017 Properties Yarmouth 851 Properties

Complexes around Massachusetts, US


Boston Day Rentals 74 Properties Proto Ames St Cambridge 31 Properties Bay 18 Properties Beacon Hill 36 Properties Braintree Inn 9 Properties North 15 Properties Wyndham Bentley Brook 31 Properties No Dennis Port 30 Properties Stay Heated 25 Properties Jiminy Peak 24 Properties Sandbars Inn North Truro 23 Properties Ski 23 Properties Brant Point 19 Properties Kendall Square 14 Properties Sconset 17 Properties
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Massachusetts Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Massachusetts?

There are a lot of options in Massachusetts. If you plan on staying in the Massachusetts area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Massachusetts:

How many vacation rentals are available in Massachusetts?

Currently, the total number of properties listed in 2026 is over 27 in the Massachusetts area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Massachusetts.