Darkest Travel - Vacation Rentals in Rocky Woods

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From US $107

         

10.0 (70 Reviews)

Apartment

Contemporary Style And Comfort Convenient To Boston And Route 128

• Air Conditioner
• Parking
• TV

• Boston
• Dedham

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From US $1,154

         

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10.0 (2 Reviews)

House

Boston Mansion Heated Pool Fire Pit Tennis

• Air Conditioner
• Parking
• Pet Friendly

• Boston
• Needham

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From US $199

         

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9.2 (1001 Reviews)

Hotel

Four Points By Sheraton Norwood

• Air Conditioner
• Parking
• Pool

• Boston
• Norwood

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From US $1,922

         

10.0 (25 Reviews)

House

Gorg 6KSF w lrg pool, sleeps 12, 4.5 baths, rec room w bar, pool table & gym.

• Air Conditioner
• Parking
• Pool

• Boston
• Walpole

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From US $660

         

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8.0 (2 Reviews)

House

Trail Access On-Site Gorgeous MCM Deck House!

• Parking
• Pet Friendly
• Accessibility

• Boston
• Dover

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From US $130

         

9.2 (1001 Reviews)

Hotel

Fairfield Inn & Suites by Marriott Boston Walpole

• Air Conditioner
• Parking
• Pool

• Boston
• Walpole

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From US $347

         

10.0 (22 Reviews)

Condo

Modern/Luxury Condo Norwood

• Air Conditioner
• Parking
• TV

• Boston
• Norwood

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From US $212

         

6.5 (297 Reviews)

Cabin

Econo Lodge Sharon - Foxborough

• Air Conditioner
• Parking
• Wheelchair Accessible

• Boston
• Sharon

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From US $122

         

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8.4 (1002 Reviews)

Hotel

Courtyard by Marriott Boston Norwood/Canton

• Air Conditioner
• Parking
• TV

• Boston
• Norwood

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From US $413

         

10.0 (9 Reviews)

Condo

Family Vacation Modern Norwood

• Air Conditioner
• Parking
• TV

• Boston
• Norwood

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From US $461

         

10.0 (4 Reviews)

House

Trail Access On-Site: Gorgeous MCM Deck House!

• Air Conditioner
• Parking
• Pet Friendly

• Boston
• Dover

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From US $304

         

10.0 (2 Reviews)

Apartment

Spacious 3-bedroom apartment in lovely Millis with AC, WiFi

• Air Conditioner
• Parking
• TV

• Boston
• Millis

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From US $1,202

         

10.0 (1 Review)

House

Lavish Boston Estate for Short or Mid Term Stays | 🏊 Pool, 🌸 Gardens, 📚 Office

• Air Conditioner
• Parking
• Pool

• Boston
• Dedham

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From US $539

         

9.8 (26 Reviews)

House

Norwood Luxe Suite- Pet friendly & Commuter friendly

• Air Conditioner
• Parking
• Pet Friendly

• Boston
• Norwood

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From US $1,192

         

New

House

The Charles Château Private Estate

• Air Conditioner
• Pet Friendly
• Balcony/Terrace

• Boston
• Dedham

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From US $370

         

New

House

Mid-Century Modern x Bohemian Home

• Air Conditioner
• Parking
• Pet Friendly

• Boston
• Natick

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New

From US $350

         

New

Cottage

Charming 2-bedroom Guest House in Dedham on Private Estate

• Air Conditioner
• Pet Friendly
• Security/Safety

• Boston
• Dedham

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New

From US $295

         

New

House

Charming 3-bedroom House- FIFA World Cup 2026 Stay

• Pet Friendly
• Security/Safety
• Child Friendly

• Boston
• Norwood

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From US $83

         

New

Condo

Extend your rest in the Wellesley Square's best

• Air Conditioner
• Parking
• TV

• Boston
• Wellesley

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From US $318

         

10.0 (23 Reviews)

House

The Cozy Colonial - 4 BDRM that's close to train and only 35 min from City!

• Air Conditioner
• Parking
• TV

• Boston
• Norwood

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From US $2,455

         

10.0 (13 Reviews)

House

Beautiful home in Wellesley's Historic district

• Air Conditioner
• Parking
• TV

• Boston
• Wellesley

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From US $118

         

10.0 (9 Reviews)

Condo

Boston - Norwood, Stylish Apartment

• Air Conditioner
• Parking
• TV

• Boston
• Norwood

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From US $119

         

10.0 (7 Reviews)

Apartment

Lovely, bright 1st fl, 1bd, fully furnished and accessorized small apartment

• Air Conditioner
• Parking
• TV

• Boston
• Norwood

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From US $96

         

10.0 (1 Review)

Apartment

Charming 3rd floor private loft space

• Air Conditioner
• Parking
• TV

• Boston
• Norwood

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